Condensed cyclic compound and organic light-emitting device including the same

ABSTRACT

A condensed cyclic compound and an organic light-emitting device, the compound being represented by Formula 1 below:

CROSS-REFERENCE TO RELATED APPLICATION

Korean Patent Application No. 10-2014-0179366, filed on Dec. 12, 2015,in the Korean Intellectual Property Office, and entitled: “CondensedCyclic Compound and Organic Light-Emitting Device Including The Same,”is incorporated by reference herein in its entirety.

BACKGROUND

1. Field

Embodiments relate to a condensed cyclic compound and an organiclight-emitting device including the same.

2. Description of the Related Art

Organic light emitting devices are self-emission devices that have wideviewing angles, high contrast ratios, short response times, andexcellent brightness, driving voltage, and response speedcharacteristics, and produce full-color images.

The organic light-emitting device may include a first electrode disposedon a substrate, and a hole transport region, an emission layer, anelectron transport region, and a second electrode, which aresequentially disposed on the first electrode. Holes provided from thefirst electrode may move toward the emission layer through the holetransport region, and electrons provided from the second electrode maymove toward the emission layer through the electron transport region.Carriers, such as holes and electrons, may be recombined in the emissionlayer to produce excitons. These excitons change from an excited stateto a ground state, thereby generating light.

SUMMARY

Embodiments are directed to a condensed cyclic compound and an organiclight-emitting device including the same

An aspect provides a condensed cyclic compound represented by Formula 1below:

wherein in Formulae 1 to 3,

X₁ is O or S;

L₁ and L₂ are each independently selected from a substituted orunsubstituted C₃-C₁₀ cycloalkylene, a substituted or unsubstitutedC₁-C₁₀ heterocycloalkylene, a substituted or unsubstitutedC₃-C₁₀cycloalkenylene, a substituted or unsubstituted C₁-C₁₀heterocycloalkenylene, a substituted or unsubstituted C₆-C₆₀ arylene, asubstituted or unsubstituted C₁-C₆₀ heteroarylene, a substituted orunsubstituted divalent non-aromatic condensed polycyclic group, and asubstituted or unsubstituted divalent non-aromatic condensedheteropolycyclic group;

a1 and a2 may be each independently selected from 0, 1, 2 and 3, when a1is 2 or more, two or more L₁ may be identical or different, and when a2is 2 or more, two or more L₂ may be identical or different.

Ar₁ to Ar₄ may be each independently selected from a substituted orunsubstituted C₃-C₁₀ cycloalkyl group, a substituted or unsubstitutedC₁-C₁₀ heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀cycloalkenyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀ arylgroup, a substituted or unsubstituted C₁-C₆₀ heteroaryl group, asubstituted or unsubstituted monovalent non-aromatic condensedpolycyclic group, and a substituted or unsubstituted monovalentnon-aromatic condensed heteropolycyclic group;

R₁ to R₁₄ may be each independently selected from a group represented byFormula 2, a group represented by Formula 3, a hydrogen, a deuterium,—F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, anamino group, an amidino group, a hydrazine group, a hydrazone group, acarboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, aphosphoric acid or a salt thereof, a substituted or unsubstituted C₁-C₆₀alkyl group, a substituted or unsubstituted C₂-C₆₀ alkenyl group, asubstituted or unsubstituted C₂-C₆₀ alkynyl group, a substituted orunsubstituted C₁-C₆₀ alkoxy group, a substituted or unsubstituted C₃-C₁₀cycloalkyl group, a substituted or unsubstituted C₁-C₁₀ heterocycloalkylgroup, a substituted or unsubstituted C₃-C₁₀cycloalkenyl group, asubstituted or unsubstituted C₁-C₁₀ heterocycloalkenyl group, asubstituted or unsubstituted C₆-C₆₀ aryl group, a substituted orunsubstituted C₆-C₆₀ aryloxy group, a substituted or unsubstitutedC₆-C₆₀ arylthio group, a substituted or unsubstituted C₁-C₆₀ heteroarylgroup, a substituted or unsubstituted monovalent non-aromatic condensedpolycyclic group, a substituted or unsubstituted monovalent non-aromaticcondensed heteropolycyclic group, and —Si(Q₁)(Q₂)(Q₃);

at least one selected from R₁ to R₁₄ is a group represented by Formula2, and at least one selected from R₁ to R₁₄ is a group represented byFormula 3:

at least one substituent of the substituted C₃-C₁₀ cycloalkylene group,substituted C₁-C₁₀ heterocycloalkylene group, substituted C₃-C₁₀cycloalkenylene group, substituted C₁-C₁₀ heterocycloalkenylene group,substituted C₆-C₆₀ arylene group, substituted C₁-C₆₀ heteroarylenegroup, substituted divalent non-aromatic condensed polycyclic group,substituted divalent non-aromatic condensed heteropolycyclic group,substituted C₁-C₆₀ alkyl group, substituted C₂-C₆₀ alkenyl group,substituted C₂-C₆₀ alkynyl group, substituted C₁-C₆₀ alkoxy group,substituted C₃-C₁₀cycloalkyl group, substituted C₁-C₁₀ heterocycloalkylgroup, substituted C₃-C₁₀ cycloalkenyl group, substituted C₁-C₁₀heterocycloalkenyl group, substituted C₆-C₆₀ aryl group, substitutedC₆-C₆₀ aryloxy group, substituted C₆-C₆₀ arylthio group, substitutedC₁-C₆₀ heteroaryl group, substituted monovalent non-aromatic condensedpolycyclic group, and substituted monovalent non-aromatic condensedheteropolycyclic group may be selected from

a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine group, a hydrazonegroup, a carboxylic acid or a salt thereof, a sulfonic acid or a saltthereof, a phosphoric acid or a salt thereof, a C₁-C₆₀ alkyl group, aC₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, and a C₁-C₆₀ alkoxy group;

a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group,and a C₁-C₆₀ alkoxy group, each substituted with at least one selectedfrom a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, anitro group, an amino group, an amidino group, a hydrazine group, ahydrazone group, a carboxylic acid group or a salt thereof, a sulfonicacid group or a salt thereof, a phosphoric acid group or a salt thereof,a C₃-C₁₀cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, aC₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀aryl group, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,a monovalent non-aromatic condensed heteropolycyclic group, and—Si(Q₁₁)(Q₁₂)(Q₁₃);

a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,and a monovalent non-aromatic heterocondensed polycyclic group;

a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, aC₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀aryl group, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,and a monovalent non-aromatic heterocondensed polycyclic group, eachsubstituted with at least one selected from a deuterium, —F, —Cl, —Br,—I, a hydroxyl group, a cyano group, a nitro group, an amino group, anamidino group, a hydrazine group, a hydrazone group, a carboxylic acidgroup or a salt thereof, a sulfonic acid group or a salt thereof, aphosphoric acid group or a salt thereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, aC₃-C₁₀cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,a monovalent non-aromatic heterocondensed polycyclic group, and—Si(Q₂₁)(Q₂₂)(Q₂₃); and

—Si(Q₃₁)(Q₃₂)(Q₃₃),

wherein Q₁ to Q₃, Q₁₁ to Q₁₃, Q₂₁ to Q₂₃, and Q₃₁ to Q₃₃ may be eachindependently selected from a hydrogen, a deuterium, —F, —Cl, —Br, —I, ahydroxyl group, a cyano group, a nitro group, an amino group, an amidinogroup, a hydrazine group, a hydrazone group, a carboxylic acid or a saltthereof, a sulfonic acid or a salt thereof, a phosphoric acid or a saltthereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynylgroup, a C₁-C₆₀ alkoxy group, a C₃-C₁₀cycloalkyl group, a C₁-C₁₀heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₁-C₆₀ heteroarylgroup, a monovalent non-aromatic condensed polycyclic group, and amonovalent non-aromatic condensed heteropolycyclic group.

Another aspect provides an organic light-emitting device that includes:a first electrode; a second electrode facing the first electrode; and anorganic layer that is disposed between the first electrode and thesecond electrode and includes an emission layer, wherein the organiclayer includes at least one of the condensed cyclic compound describedabove.

BRIEF DESCRIPTION OF THE DRAWING

Features will be apparent to those of skill in the art by describing indetail exemplary embodiments with reference to the attached drawings inwhich:

FIG. 1 illustrates is a schematic view of an organic light-emittingdevice according to an embodiment.

DETAILED DESCRIPTION

Example embodiments will now be described more fully hereinafter withreference to the accompanying drawing; however, they may be embodied indifferent forms and should not be construed as limited to theembodiments set forth herein. Rather, these embodiments are provided sothat this disclosure will be thorough and complete, and will fullyconvey exemplary implementations to those skilled in the art.

In the drawing FIGURE, the dimensions of layers and regions may beexaggerated for clarity of illustration. Like reference numerals referto like elements throughout.

A condensed cyclic compound according to an embodiment may berepresented by Formula 1 below.

X₁ in Formula 1 may be, e.g., O or S. In an implementation, X₁ may be O.

R₁ to R₁₄ in Formula 1 may each independently be selected from orinclude, e.g., a group represented by Formula 2, a hydrogen, adeuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine group, a hydrazonegroup, a carboxylic acid or a salt thereof, a sulfonic acid or a saltthereof, a phosphoric acid or a salt thereof, a substituted orunsubstituted C₁-C₆₀ alkyl group, a substituted or unsubstituted C₂-C₆₀alkenyl group, a substituted or unsubstituted C₂-C₆₀ alkynyl group, asubstituted or unsubstituted C₁-C₆₀ alkoxy group, a substituted orunsubstituted C₃-C₁₀ cycloalkyl group, a substituted or unsubstitutedC₁-C₁₀ heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀cycloalkenyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀ arylgroup, a substituted or unsubstituted C₆-C₆₀ aryloxy group, asubstituted or unsubstituted C₆-C₆₀ arylthio group, a substituted orunsubstituted C₁-C₆₀ heteroaryl group, a substituted or unsubstitutedmonovalent non-aromatic condensed polycyclic group, a substituted orunsubstituted monovalent non-aromatic condensed heteropolycyclic group,and —Si(Q₁)(Q₂)(Q₃).

In an implementation, at least one of R₁ to R₁₄ in Formula 1 may be agroup represented by the following Formula 2, and at least one of R₁ toR₁₄ may be a group represented by the following Formula 3.

In Formulae 2 and 3,

L₁ and L₂ may each independently be selected from or include, e.g., asubstituted or unsubstituted C₃-C₁₀ cycloalkylene, a substituted orunsubstituted C₁-C₁₀ heterocycloalkylene, a substituted or unsubstitutedC₃-C₁₀ cycloalkenylene, a substituted or unsubstituted C₁-C₁₀heterocycloalkenylene, a substituted or unsubstituted C₆-C₆₀ arylene, asubstituted or unsubstituted C₁-C₆₀ heteroarylene, a substituted orunsubstituted divalent non-aromatic condensed polycyclic group, and asubstituted or unsubstituted divalent non-aromatic condensedheteropolycyclic group.

For example, L₁ to L₂ in Formulae 2 and 3 may each independently beselected from:

a phenylene group, a pentalenylene group, an indenylene group, anaphthylene group, an azulenylene group, a heptalenylene group, anindacenylene group, an acenaphthylene group, a fluorenylene group, aspiro-fluorenylene group, a benzofluorenylene group, adibenzofluorenylene group, a phenalenylene group, a phenanthrenylenegroup, an anthracenylene group, a fluoranthenylene group, atriphenylenylene group, a pyrenylene group, a chrysenylene group, anaphthacenylene group, a picenylene group, a perylenylene group, apentaphenylene group, a hexacenylene group, a pentacenylene group, arubicenylene group, a coronenylene group, an ovalenylene group, apyrrolylene group, a thiophenylene group, a furanylene group, animidazolylene group, a pyrazolylene group, a thiazolylene group, anisothiazolylene group, an oxazolylene group, a isoxazolylene group, apyridinylene group, a pyrazinylene group, a pyrimidinylene group, apyridazinylene group, an isoindolylene group, an indolylene group, anindazolylene group, a purinylene group, a quinolinylene group, anisoquinolinylene group, a benzoquinolinylene group, a phthalazinylenegroup, a naphthyridinylene group, a quinoxalinylene group, aquinazolinylene group, a cinnolinylene group, a carbazolylene group, aphenanthridinylene group, an acridinylene group, a phenanthrolinylenegroup, a phenazinylene group, a benzoimidazolylene group, abenzofuranylene group, a benzothiophenylene group, anisobenzothiazolylene group, a benzoxazolylene group, anisobenzoxazolylene group, a triazolylene group, a tetrazolylene group,an oxadiazolylene group, a triazinylene group, a dibenzofuranylenegroup, a dibenzothiophenylene group, a benzocarbazolylene group, adibenzocarbazolylene group, a thiadiazolylene group, animidazopyridinylene group, and an imidazopyrimidinylene group; and

a phenylene group, a pentalenylene group, an indenylene group, anaphthylene group, an azulenylene group, a heptalenylene group, anindacenylene group, an acenaphthylene group, a fluorenylene group, aspiro-fluorenylene group, a benzofluorenylene group, adibenzofluorenylene group, a phenalenylene group, a phenanthrenylenegroup, an anthracenylene group, a fluoranthenylene group, atriphenylenylene group, a pyrenylene group, a chrysenylene group, anaphthacenylene group, a picenylene group, a perylenylene group, apentaphenylene group, a hexacenylene group, a pentacenylene group, arubicenylene group, a coronenylene group, ovalenylene group, apyrrolylene group, a thiophenylene group, a furanylene group, animidazolylene group, a pyrazolylene group, a thiazolylene group, anisothiazolylene group, an oxazolylene group, a isoxazolylene group, apyridinylene group, a pyrazinylene group, a pyrimidinylene group, apyridazinylene group, an isoindolylene group, an indolylene group, anindazolylene group, a purinylene group, a quinolinylene group, anisoquinolinylene group, a benzoquinolinylene group, a phthalazinylenegroup, a naphthyridinylene group, a quinoxalinylene group, aquinazolinylene group, a cinnolinylene group, a carbazolylene group, aphenanthridinylene group, an acridinylene group, a phenanthrolinylenegroup, a phenazinylene group, a benzoimidazolylene group, abenzofuranylene group, a benzothiophenylene group, anisobenzothiazolylene group, a benzoxazolylene group, anisobenzoxazolylene group, a triazolylene group, a tetrazolylene group,an oxadiazolylene group, a triazinylene group, a dibenzofuranylenegroup, a dibenzothiophenylene group, a benzocarbazolylene group, adibenzocarbazolylene group, a thiadiazolylene group, animidazopyridinylene group, and an imidazopyrimidinylene group, eachsubstituted with at least one selected from a deuterium, —F, —Cl, —Br,—I, a hydroxyl group, a cyano group, a nitro group, an amino group, anamidino group, a hydrazine group, a hydrazone group, a carboxylic acidor a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acidor a salt thereof, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, acyclopentyl group, a cyclohexyl group, a cycloheptyl group, acyclopentenyl group, a cyclohexenyl group, a phenyl group, a pentalenylgroup, an indenyl group, a naphthyl group, an azulenyl group, aheptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenylgroup, a spiro-fluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, ananthracenyl group, a fluoranthenyl group, a triphenylenyl group, apyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group,a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenylgroup, a rubicenyl group, a coronenyl group, an ovalenyl group, apyrrolyl group, a thiophenyl group, a furanyl group, an imidazolylgroup, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, anoxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinylgroup, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, anindolyl group, an indazolyl group, a purinyl group, a quinolinyl group,an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, anaphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, acinnolinyl group, a carbazolyl group, a phenanthridinyl group, anacridinyl group, a phenanthrolinyl group, a phenazinyl group, abenzoimidazolyl group, a benzofuranyl group, a benzothiophenyl group, anisobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group,a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinylgroup, a dibenzofuranyl group, a dibenzothiophenyl group, abenzocarbazolyl group, a dibenzocarbazolyl group, a thiadiazolyl group,an imidazopyridinyl group, and an imidazopyrimidinyl group.

In an embodiment, L₁ and L₂ in Formulae 2 and 3 may each independentlybe a group represented by one of the following Formulae 3-1 to 3-35.

In Formulae 3-1 to 3-35,

Y₁ may be, e.g., O, S, C(Z₃)(Z₄), N(Z₅), or Si(Z₆)(Z₇);

Z₁ to Z₇ may each independently be selected from, e.g., a hydrogen, adeuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine group, a hydrazonegroup, a carboxylic acid or a salt thereof, a sulfonic acid or a saltthereof, a phosphoric acid or a salt thereof, a C₁ to C₂₀ alkyl group, aC₁ to C₂₀ alkoxy group, a phenyl group, a naphthyl group, a fluorenylgroup, a spiro-fluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, apyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group,a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, anisoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, acarbazolyl group, and a triazinyl group,

d1 may be an integer selected from 1, 2, 3, and 4, d2 may be an integerselected from 1, 2, and 3, d3 may be an integer selected from 1, 2, 3,4, 5, and 6, d4 may be an integer selected from 1, 2, 3, 4, 5, 6, 7, and8, d5 may be 1 or 2, d6 may be an integer selected from 1, 2, 3, 4, and5, and * and *′ indicate binding sites to a neighboring atom.

In some embodiments, L₁ and L₂ in Formulae 2 and 3 may eachindependently be selected from:

a phenylene group, a naphthylene group, a pyridinylene group, adibenzofuranylene group, and a dibenzothiophenylene group; and

a phenylene group, a naphthylene group, a pyridinylene group, adibenzofuranylene group, and a dibenzothiophenylene group, eachsubstituted with at least one selected from a deuterium, —F, —Cl, —Br,—I, a hydroxyl group, a cyano group, a nitro group, an amino group, anamidino group, a hydrazine group, a hydrazone group, a carboxylic acidor a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acidor a salt thereof, a C1-C10 alkyl group, a phenyl group, a naphthylgroup, a pyridinyl group, a pyrimidinyl group, and a triazinyl group.

In some embodiments, L₁ and L₂ in Formulae 2 and 3 may eachindependently be a group represented by one of the following Formulae4-1 to 4-29.

* and *′ in Formulae 4-1 to 4-29 each indicate a binding site to aneighboring atom.

a1 and a2 in Formulae 2 and 3 may be selected from 0, 1, 2, and 3. a1indicates the number of L₁ in Formula 2, and when a1 is 2 or more, aplurality of L₁ may be identical or different. For example, when a1 is0, *-(L₁)_(a1)-*′ is a single bond. a2 indicates the number of L₂ inFormula 3, and when a2 is 2 or more, a plurality of L₂ may be identicalor different. When a2 is 0, *-(L₂)_(a2)-*′ is a single bond. In someembodiments, a1 and a2 may be each independently 0, 1, or 2. In someembodiments, a1 and a2 may be each independently 0 or 1.

Ar₁ to Ar₄ in Formulae 2 and 3 may each independently be selected fromor include, e.g., a substituted or unsubstituted C₃-C₁₀ cycloalkylene, asubstituted or unsubstituted C₁-C₁₀ heterocycloalkylene, a substitutedor unsubstituted C₃-C₁₀ cycloalkenylene, a substituted or unsubstitutedC₁-C₁₀ heterocycloalkenylene, a substituted or unsubstituted C₆-C₆₀arylene, a substituted or unsubstituted C₁-C₆₀ heteroarylene, asubstituted or unsubstituted divalent non-aromatic condensed polycyclicgroup, and a substituted or unsubstituted divalent non-aromaticcondensed heteropolycyclic group.

For example, Ar₁ to Ar₄ in Formulae 2 and 3 may each independently beselected from:

a phenyl group, a pentalenyl group, an indenyl group, a naphthyl group,an azulenyl group, a heptalenyl group, an indacenyl group, anacenaphthyl group, a fluorenyl group, a spiro-fluorenyl group, abenzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, aphenanthrenyl group, an anthracenyl group, a fluoranthenyl group, atriphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenylgroup, a picenyl group, a perylenyl group, a pentaphenyl group, ahexacenyl group, a pentacenyl group, a rubicenyl group, a coronenylgroup, an ovalenyl group, a pyrrolyl group, a thiophenyl group, afuranyl group, an imidazolyl group, a pyrazolyl group, a thiazolylgroup, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, apyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, an isoindolyl group, an indolyl group, an indazolyl group, apurinyl group, a quinolinyl group, an isoquinolinyl group, abenzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, aquinoxalinyl group, a quinazolinyl group, a cinnolinyl group, acarbazolyl group, a phenanthridinyl group, an acridinyl group, aphenanthrolinyl group, a phenazinyl group, a benzoimidazolyl group, abenzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group,a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, atetrazolyl group, an oxadiazolyl group, a triazinyl group, adibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolylgroup, a dibenzocarbazolyl group, a dibenzosilolyl group), athiadiazolyl group, an imidazopyridinyl group, and an imidazopyrimidinylgroup;

a phenyl group, a pentalenyl group, an indenyl group, a naphthyl group,an azulenyl group, a heptalenyl group, an indacenyl group, anacenaphthyl group, a fluorenyl group, a spiro-fluorenyl group, abenzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, aphenanthrenyl group, an anthracenyl group, a fluoranthenyl group, atriphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenylgroup, a picenyl group, a perylenyl group, a pentaphenyl group, ahexacenyl group, a pentacenyl group, a rubicenyl group, a coronenylgroup, an ovalenyl group, a pyrrolyl group, a thiophenyl group, afuranyl group, an imidazolyl group, a pyrazolyl group, a thiazolylgroup, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, apyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, an isoindolyl group, an indolyl group, an indazolyl group, apurinyl group, a quinolinyl group, an isoquinolinyl group, abenzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, aquinoxalinyl group, a quinazolinyl group, a cinnolinyl group, acarbazolyl group, a phenanthridinyl group, an acridinyl group, aphenanthrolinyl group, a phenazinyl group, a benzoimidazolyl group, abenzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group,a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, atetrazolyl group, an oxadiazolyl group, a triazinyl group, adibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolylgroup, a dibenzosilolyl group), a dibenzocarbazolyl group, athiadiazolyl group, an imidazopyridinyl group, and an imidazopyrimidinylgroup, each substituted with at least one selected from a deuterium, —F,—Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an aminogroup, an amidino group, a hydrazine group, a hydrazone group, acarboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, aphosphoric acid or a salt thereof, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxygroup, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, acyclopentenyl group, a cyclohexenyl group, a phenyl group, a pentalenylgroup, an indenyl group, a naphthyl group, an azulenyl group, aheptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenylgroup, a spiro-fluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, ananthracenyl group, a fluoranthenyl group, a triphenylenyl group, apyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group,a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenylgroup, a rubicenyl group, a coronenyl group, an ovalenyl group, apyrrolyl group, a thiophenyl group, a furanyl group, an imidazolylgroup, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, anoxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinylgroup, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, anindolyl group, an indazolyl group, a purinyl group, a quinolinyl group,an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, anaphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, acinnolinyl group, a carbazolyl group, a phenanthridinyl group, anacridinyl group, a phenanthrolinyl group, a phenazinyl group, abenzoimidazolyl group, a benzofuranyl group, a benzothiophenyl group, anisobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group,a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinylgroup, a dibenzofuranyl group, a dibenzothiophenyl group, abenzocarbazolyl group and a dibenzocarbazolyl group, a thiadiazolylgroup, an imidazopyridinyl group, an imidazopyrimidinyl group, and—Si(Q₃₁)(Q₃₂)(Q₃₃); and

Q₃₁ to Q₃₃ may each independently be selected from a C₁-C₁₀ alkyl group,a C₁-C₁₀ alkoxy group, a phenyl group, a naphthyl group, a fluorenylgroup, a spiro-fluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, atriphenylenyl group, a pyrenyl group, a chrysenyl group, a pyrrolylgroup, a thiophenyl group, a furanyl group, an imidazolyl group, apyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolylgroup, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, apyrimidinyl group, a pyridazinyl group, a quinolinyl group, anisoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, aquinazolinyl group, a carbazolyl group, a phenanthrolinyl group, abenzoimidazolyl group, a benzofuranyl group, a benzothiophenyl group, anisobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group,a triazolyl group, an oxadiazolyl group, a triazinyl group, adibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolylgroup, a dibenzocarbazolyl group, a dibenzosilolyl group, a thiadiazolylgroup, an imidazopyridinyl group, and an imidazopyrimidinyl group.

In some embodiments, Ar₁ to Ar₄ in Formulae 2 and 3 may eachindependently be selected from:

a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenylgroup, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenylgroup, an anthracenyl group, a triphenylenyl group, a pyrenyl group, achrysenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group,an imidazolyl group, a pyrazolyl group, a thiazolyl group, anisothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinylgroup, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, aquinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, aquinoxalinyl group, a quinazolinyl group, a carbazolyl group, abenzoimidazolyl group, a benzofuranyl group, a benzothiophenyl group, anisobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group,an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, adibenzothiophenyl group, an imidazopyridinyl group, and animidazopyrimidinyl group; and

a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenylgroup, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenylgroup, an anthracenyl group, a triphenylenyl group, a pyrenyl group, achrysenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group,an imidazolyl group, a pyrazolyl group, a thiazolyl group, anisothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinylgroup, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, aquinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, aquinoxalinyl group, a quinazolinyl group, a carbazolyl group, abenzoimidazolyl group, a benzofuranyl group, a benzothiophenyl group, anisobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group,an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, adibenzothiophenyl group, an imidazopyridinyl group, and animidazopyrimidinyl group, each substituted with at least one selectedfrom a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, anitro group, an amino group, an amidino group, a hydrazine group, ahydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid ora salt thereof, a phosphoric acid or a salt thereof, a C₁-C₁₀ alkylgroup, a C₁-C₁₀ alkoxy group, a phenyl group, a naphthyl group, afluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, atriphenylenyl group, a pyrenyl group, a chrysenyl group, a pyrrolylgroup, a thiophenyl group, a furanyl group, an imidazolyl group, apyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolylgroup, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, apyrimidinyl group, a pyridazinyl group, a quinolinyl group, anisoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, aquinazolinyl group, a carbazolyl group, a benzoimidazolyl group, abenzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group,a benzoxazolyl group, an isobenzoxazolyl group, an oxadiazolyl group, atriazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, animidazopyridinyl group, an imidazopyrimidinyl group, and—Si(Q₃₁)(Q₃₂)(Q₃₃),

Q₃₁ to Q₃₃ may each independently be selected from a C₁-C₁₀ alkyl group,a C₁-C₁₀ alkoxy group, a phenyl group, and a naphthyl group.

In some embodiments, Ar₁ to Ar₄ in Formulae 2 and 3 may eachindependently be selected from:

a phenyl group, a naphthyl group, a fluorenyl group, a phenanthrenylgroup, a pyridinyl group, a pyrimidinyl group, a triazinyl group, adibenzofuranyl group, and a dibenzothiophenyl group; and

a phenyl group, a naphthyl group, a fluorenyl group, a phenanthrenylgroup, a pyridinyl group, a pyrimidinyl group, a triazinyl group, adibenzofuranyl group, and a dibenzothiophenyl group, each substitutedwith at least one selected from a deuterium, —F, —Cl, —Br, —I, ahydroxyl group, a cyano group, a nitro group, an amino group, an amidinogroup, a hydrazine group, a hydrazone group, a carboxylic acid or a saltthereof, a sulfonic acid or a salt thereof, a phosphoric acid or a saltthereof, a C₁-C₁₀ alkyl group, a C₁-C₁₀ alkoxy group, a phenyl group, anaphthyl group, a fluorenyl group, a phenanthrenyl group, a pyridinylgroup, a pyrimidinyl group, a triazinyl group, a dibenzofuranyl group, adibenzothiophenyl group, and —Si(Q₃₁)(Q₃₂)(Q₃₃),

Q₃₁ to Q₃₃ may each independently be selected from a C₁-C₁₀ alkyl group,a C₁-C₁₀alkoxy group, a phenyl group, and a naphthyl group.

In an implementation, R₁ to R₁₄ in Formula 1 may each independently beselected from:

a group represented by Formula 2, a group represented by Formula 3, ahydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyanogroup, a nitro group, an amino group, an amidino group, a hydrazinegroup, a hydrazone group, a carboxylic acid or a salt thereof, asulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, aC₁-C₂₀ alkyl group, and a C₁-C₂₀ alkoxy group;

a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenylgroup, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenylgroup, an anthracenyl group, a triphenylenyl group, a pyrenyl group, achrysenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group,an imidazolyl group, a pyrazolyl group, a thiazolyl group, anisothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinylgroup, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, aquinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, aquinoxalinyl group, a quinazolinyl group, a carbazolyl group, abenzoimidazolyl group, a benzofuranyl group, a benzothiophenyl group, anisobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group,an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, adibenzothiophenyl group, an imidazopyridinyl group, and animidazopyrimidinyl group;

a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenylgroup, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenylgroup, an anthracenyl group, a triphenylenyl group, a pyrenyl group, achrysenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group,an imidazolyl group, a pyrazolyl group, a thiazolyl group, anisothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinylgroup, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, aquinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, aquinoxalinyl group, a quinazolinyl group, a carbazolyl group, abenzoimidazolyl group, a benzofuranyl group, a benzothiophenyl group, anisobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group,an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, adibenzothiophenyl group, an imidazopyridinyl group, and animidazopyrimidinyl group, each substituted with at least one selectedfrom a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, anitro group, an amino group, an amidino group, a hydrazine group, ahydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid ora salt thereof, a phosphoric acid or a salt thereof, a C₁-C₁₀ alkylgroup, a C₁-C₁₀ alkoxy group, a phenyl group, a naphthyl group, afluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, atriphenylenyl group, a pyrenyl group, a chrysenyl group, a pyrrolylgroup, a thiophenyl group, a furanyl group, an imidazolyl group, apyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolylgroup, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, apyrimidinyl group, a pyridazinyl group, a quinolinyl group, anisoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, aquinazolinyl group, a carbazolyl group, a benzoimidazolyl group, abenzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group,a benzoxazolyl group, an isobenzoxazolyl group, an oxadiazolyl group, atriazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, animidazopyridinyl group, an imidazopyrimidinyl group, and—Si(Q₃₁)(Q₃₂)(Q₃₃); and

—Si(Q₁)(Q₂)(Q₃),

wherein Q₁ to Q₃ and Q₃₁ to Q₃₃ may be each independently selected froma C₁-C₁₀ alkyl group, a C₁-C₁₀ alkoxy group, a phenyl group, and anaphthyl group.

For example, R₁ to R₁₄ in Formula 1 may each independently be selectedfrom

a group represented by Formula 2, a group represented by Formula 3, ahydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyanogroup, a nitro group, an amino group, an amidino group, a hydrazinegroup, a hydrazone group, a carboxylic acid or a salt thereof, asulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, aC₁-C₁₀ alkyl group, and a C₁-C₁₀alkoxy group;

a phenyl group, a naphthyl group, a pyrimidinyl group, and a triazinylgroup;

a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinylgroup, and a triazinyl group, each substituted with at least oneselected from a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyanogroup, a nitro group, an amino group, an amidino group, a hydrazinegroup, a hydrazone group, a carboxylic acid or a salt thereof, asulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, aC₁-C₁₀ alkyl group, a C₁-C₁₀ alkoxy group, a phenyl group, a naphthylgroup, a pyridinyl group, a pyrimidinyl group, a triazinyl group, and—Si(Q₃₁)(Q₃₂)(Q₃₃); and

—Si(Q)(Q₂)(Q₃),

wherein Q₁ to Q₃ and Q₃₁ to Q₃₃ may each independently be selected froma C₁-C₁₀ alkyl group, a C₁-C₁₀ alkoxy group, a phenyl group, and anaphthyl group.

In an implementation, Ar₁ to Ar₄ may each independently be a grouprepresented by one of the following Formulae 5-1 to 5-43.

In an implementation, R₁ to R₁₄ may each independently be selected froma group represented by Formula 2, a group represented by Formula 3, ahydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyanogroup, a nitro group, an amino group, an amidino group, a hydrazinegroup, a hydrazone group, a carboxylic acid or a salt thereof, asulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, aC₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, —Si(Q₁)(Q₂)(Q₃), and a grouprepresented by one of Formulae 5-1 to 5-43, and Q₁ to Q₃ may eachindependently be selected from a C₁-C₁₀ alkyl group, a C₁-C₁₀ alkoxygroup, a phenyl group, and a naphthyl group.

In Formulae 5-1 to 5-43,

Y₃₁ may be O, S, C(Z₃₃)(Z₃₄), N(Z₃₅), or Si(Z₃₆)(Z₃₇);

Z₃₁ to Z₃₇ may each independently be selected from a hydrogen, adeuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine group, a hydrazonegroup, a carboxylic acid or a salt thereof, a sulfonic acid or a saltthereof, a phosphoric acid or a salt thereof, a C₁ to C₂₀ alkyl group, aC₁ to C₂₀ alkoxy group, a phenyl group, a naphthyl group, a fluorenylgroup, a spiro-fluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, apyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group,a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, anisoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, acarbazolyl group, and a triazinyl group,

e3 may be an integer selected from 1, 2, and 3, e4 may be an integerselected from 1, 2, 3, and 4, e5 may be an integer selected from 1, 2,3, 4, and 5, e6 may be an integer selected from 1, 2, 3, 4, 5, and 6, e7may be an integer selected from 1, 2, 3, 4, 5, 6, and 7, e8 may be aninteger selected from 1, 2, 3, 4, 5, 6, 7, and 8, e9 may be an integerselected from 1, 2, 3, 4, 5, 6, 7, 8, and 9, and * indicates a bindingsite to a neighboring atom.

In some embodiments, regarding Formulae 1 to 3,

Ar₁ to Ar₄ may each independently be a group represented by one of thefollowing Formulae 6-1 to 6-40, and

R₁ to R₁₄ may each independently be selected from a group represented byFormula 2, a group represented by Formula 3, a hydrogen, a deuterium,—F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, anamino group, an amidino group, a hydrazine group, a hydrazone group, acarboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, aphosphoric acid or a salt thereof, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxygroup, —Si(Q₁)(Q₂)(Q₃), a phenyl group, a naphthyl group, a pyridinylgroup, a pyrimidinyl group, and a triazinyl group, and Q₁ to Q₃ may beeach independently selected from a C₁-C₁₀ alkyl group, a C₁-C₁₀ alkoxygroup, a phenyl group, and a naphthyl group.

* in Formulae 6-1 to 6-40 indicates a binding site to a neighboringatom.

In an implementation, two substituents of R₁ to R₁₂ in Formula 1 mayeach independently be selected from a group represented by Formula 2 anda group represented by Formula 3.

For example, the condensed cyclic compound represented by Formula 1 maybe represented by one of the following Formulae 1-1 to 1-8.

Descriptions of X₁, L₁, L₂, a₁, a₂, Ar₁ to Ar₄, and R₁ to R₁₄ in Formula1-1 to Formula 1-8 may be the same as described above.

In some embodiments, regarding Formulae 1-1 to 1-8,

a1 may be 0 and a2 may be 0;

a1 may be 0 and a2 may be 1 or 2;

a1 may be 1 or 2 and a2 may be 0;

a1 may be 1 and a2 may be 1;

a1 may be 1 and a2 may be 2;

a1 may be 2 and a2 may be 1; or

a1 may be 2 and a2 may be 2.

In some embodiments, regarding Formulae 1-1 to 1-8,

a1 may be 0 and a2 may be 0;

a1 may be 0 and a2 may be 1;

a1 may be 1 and a2 may be 0; or

a1 may be 1 and a2 may be 1.

In some embodiments, regarding Formulae 1-1 to 1-8,

Ar₁=Ar₂=Ar₃=Ar₄

Ar₁=Ar₃ and, Ar₂=Ar₄ and, Ar₂≠Ar₃;

Ar₁=Ar₃ and, Ar₂≠Ar₄ and, Ar₂≠Ar₃; or

Ar₁≠Ar₂≠Ar₃≠Ar₄.

In some embodiments, regarding Formulae 1-1 to 1-8,

R₁ to R₁₄ may each independently be selected from a hydrogen, adeuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine group, a hydrazonegroup, a carboxylic acid or a salt thereof, a sulfonic acid or a saltthereof, a phosphoric acid or a salt thereof, a C₁-C₂₀ alkyl group, aC₁-C₂₀ alkoxy group, a phenyl group, a naphthyl group, a pyridinylgroup, a pyrimidinyl group, and a triazinyl group,

L₁ and L₂ may each independently be a group represented by one ofFormulae 3-1 to 3-35,

a1 and a2 may each independently be 0, 1, or 2;

Ar₁ to Ar₄ may each independently be a group represented by one ofFormula 5-1 to 5-43.

In some embodiments, regarding Formulae 1-1 to 1-8,

R₁ to R₄, R₆ to R₁₂, and R₁₄ may be hydrogens,

L₁ and L₂ may each independently be a group represented by one ofFormulae 4-1 to 4-29,

a1 and a2 may each independently be 0 or 1,

Ar₁ to Ar₄ may each independently be a group represented by one ofFormula 6-1 to 6-40.

In some embodiments, the condensed cyclic compound represented byFormula 1 may be represented by one of Formulae 1-1(1) to 1-1(4) below.

Descriptions of X₁, L₁, L₂, Ar₁ to Ar₄, R₁ to R₄, R₆ to R₁₂ and R₁₄ inFormulae 1-1(1) to 1-1(4) may be the same as described above.

For example, the condensed cyclic compound represented by Formula 1 maybe one of Compounds 1 to 104 below.

The condensed cyclic compound represented by Formula 1 may have an aminegroup and a boryl group in its molecular structure. Due to the inclusionof these groups, the condensed cyclic compound may have a high glasstransition temperature (Tg) or a high melting point. Accordingly, a heatresistance to Joule heat (which may occur inside an organic layer orbetween an organic layer and an electrode) and a resistance to hightemperature environments may increase, and thus, an organiclight-emitting device including the condensed cyclic compoundrepresented by Formula 1 may have high durability during preserving anddriving.

A boron atom has an empty p orbital. Accordingly, an electronwithdrawing property of the condensed cyclic compound represented byFormula 1 having a boryl group in its molecular structure may beincreased, and thus, an electron injection capability and an electrontransport capability may be increased. Thus, an organic light-emittingdevice including the condensed cyclic compound may have high luminescentefficiency.

A core of the condensed cyclic compound represented by Formula 1 mayhave many n-conjugation systems. Accordingly, the condensed cycliccompound may have high luminescent efficiency. Also, the core of thecondensed cyclic compound represented by Formula 1 may include an oxygenatom (which is a hetero atom), and due to the interaction with a borylgroup or an amine group, the electron injection capability and anelectron transport capability may all be increased.

The condensed cyclic compound represented by Formula 1 may besynthesized by using a suitable organic synthetic method. A synthesismethod of the condensed cyclic compound may be recognizable in view ofthe following embodiments.

At least one of the condensed cyclic compound of Formula 1 may be usedor included between a pair of electrodes of an organic light-emittingdevice. In some embodiments, the condensed cyclic compound may beincluded in a hole transport region, e.g., a hole transport layer. Insome embodiments, the condensed cyclic compound may be included in anemission layer. Accordingly, an organic light-emitting device accordingto an embodiment may include, e.g., a first electrode; a secondelectrode facing the first electrode; and an organic layer that isdisposed between the first electrode and the second electrode andincludes an emission layer, wherein the organic layer includes at leastone of the condensed cyclic compounds described above.

The expression that “(an organic layer) includes at least one condensedcyclic compound” used herein may include a case in which “(an organiclayer) includes identical condensed cyclic compounds represented byFormula 1 and a case in which (an organic layer) includes two or moredifferent condensed cyclic compounds represented by Formula 1.

For example, the organic layer may include, as the condensed cycliccompound, only Compound 1. In this regard, Compound 1 may exist in anemission layer of the organic light-emitting device. In someembodiments, the organic layer may include, as the condensed cycliccompound, Compound 1 and Compound 2. In this regard, Compound 1 andCompound 2 may exist in an identical layer (for example, Compound 1 andCompound 2 may all exist in an emission layer), or different layers (forexample, Compound 1 may exist in a hole transport layer and Compound 2may exist in an emission layer).

The organic layer may include, e.g., i) a hole transport region that isdisposed between the first electrode (anode) and the emission layer andincludes at least one of a hole injection layer, a hole transport layer,a buffer layer, and an electron blocking layer, and ii) an electrontransport region that is disposed between the emission layer and thesecond electrode (cathode) and includes at least one selected from ahole blocking layer, an electron transport layer, and an electroninjection layer. At least one of the hole transport region and theemission layer may include at least one of the condensed cyclic compoundrepresented by Formula 1. For example, the hole transport region mayinclude the hole transport layer, and the hole transport layer mayinclude at least one of the condensed cyclic compound represented byFormula 1.

The term “organic layer” used herein refers to a single layer and/or aplurality of layers disposed between the first electrode and the secondelectrode of an organic light-emitting device. A material included inthe “organic layer” is not limited to an organic material.

FIG. 1 illustrates a schematic view of an organic light-emitting device10 according to an embodiment. The organic light-emitting device 10 mayinclude a first electrode 110, an organic layer 150, and a secondelectrode 190.

Hereinafter, the structure of an organic light-emitting device accordingto an embodiment and a method of manufacturing an organic light-emittingdevice according to an embodiment will be described in connection withFIG. 1.

In FIG. 1, a substrate may be additionally disposed under the firstelectrode 110 or above the second electrode 190. The substrate may be aglass substrate or transparent plastic substrate, each with excellentmechanical strength, thermal stability, transparency, surfacesmoothness, ease of handling, and water-resistance.

The first electrode 110 may be formed by depositing or sputtering amaterial for forming the first electrode on the substrate. When thefirst electrode 10 is an anode, the material for the first electrode maybe selected from materials with a high work function to facilitate holeinjection. The first electrode 110 may be a reflective electrode or atransmissive electrode. The material for the first electrode may be atransparent and highly conductive material, and examples of such amaterial may include indium tin oxide (ITO), indium zinc oxide (IZO),tin oxide (SnO₂), and zinc oxide (ZnO). When the first electrode 110 isa semi-transmissive electrode or a reflective electrode, as a materialfor forming the first electrode, at least one of magnesium (Mg),aluminum (Al), aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium(Mg—In), magnesium-silver (Mg—Ag) may be used.

The first electrode 110 may have a single-layer structure, or amulti-layer structure including two or more layers. For example, thefirst electrode 110 may have a three-layered structure of ITO/Ag/ITO.

An organic layer 150 may be disposed on the first electrode 110. Theorganic layer 150 may include an emission layer.

The organic layer 150 may further include a hole transport regiondisposed between the first electrode and the emission layer, and anelectron transport region disposed between the emission layer and thesecond electrode.

The hole transport region may include at least one selected from a holeinjection layer (HIL), a hole transport layer (HTL), a buffer layer, andan electron blocking layer (EBL), and the electron transport region mayinclude at least one selected from a hole blocking layer (HBL), anelectron transport layer (ETL), and an electron injection layer (EIL).

The hole transport region may have a single-layered structure formed ofa single material, a single-layered structure formed of a plurality ofdifferent materials, or a multi-layered structure having a plurality oflayers formed of a plurality of different materials.

For example, the hole transport region may have a single-layeredstructure formed of a plurality of different materials, or a structureof hole injection layer/hole transport layer, a structure of holeinjection layer/hole transport layer/buffer layer, a structure of holeinjection layer/buffer layer, a structure of hole transport layer/bufferlayer, or a structure of hole injection layer/hole transportlayer/electron blocking layer, wherein layers of each structure aresequentially stacked from the first electrode 110 in this stated order.

When the hole transport region includes a hole injection layer, the holeinjection layer may be formed on the first electrode 110 by usingvarious methods, such as vacuum deposition, spin coating casting, aLangmuir-Blodgett (LB) method, ink-jet printing, laser-printing, orlaser-induced thermal imaging.

When a hole injection layer is formed by vacuum deposition, for example,the vacuum deposition may be performed at a temperature of a depositiontemperature of about 100 to about 500° C. at a vacuum degree of about10⁻⁸ to about 10⁻³ torr, and at a deposition rate of about 0.01 to about100 Å/sec in consideration of a compound for a hole injection layer tobe deposited, and the structure of a hole injection layer to be formed.

When a hole injection layer is formed by spin coating, the spin coatingmay be performed at a coating rate of about 2000 rpm to about 5000 rpm,and at a temperature of about 80° C. to 200° C. in consideration of acompound for a hole injection layer to be deposited, and the structureof a hole injection layer to be formed.

When the hole transport region includes a hole transport layer, the holetransport layer may be formed on the first electrode 110 or the holeinjection layer by using various methods, such as vacuum deposition,spin coating, casting, a LB method, ink-jet printing, laser-printing, orlaser-induced thermal imaging. When the hole transport layer is formedby vacuum deposition or spin coating, deposition and coating conditionsfor the hole transport layer may be determined by referring to thedeposition and coating conditions for the hole injection layer.

The hole transport region may include the condensed cyclic compoundrepresented by Formula 1. For example, the hole transport region mayinclude the hole transport layer, wherein the hole transport layerincludes the condensed cyclic compound represented by Formula 1.

The hole transport region may include at least one selected fromm-MTDATA, TDATA, 2-TNATA, NPB, β-NPB, TPD, Spiro-TPD, Spiro-NPB, α-NPB,TAPC, HMTPD, 4,4′,4″-tris(N-carbazolyl)triphenylamine (TCTA),polyaniline/dodecylbenzenesulfonic acid (Pani/DBSA),poly(3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate) (PEDOT/PSS),polyaniline/camphor sulfonicacid (PANI/CSA),(polyaniline)/poly(4-styrenesulfonate) (Pani/PSS), a compoundrepresented by Formula 201 below, and a compound represented by Formula202 below:

In Formulae 201 and 202,

L₂₀₁ to L₂₀₅ may be the same as explained in connection with L₁;

xa1 to xa4 may each independently be selected from 0, 1, 2, and 3;

xa5 may be selected from 1, 2, 3, 4, and 5; and

R₂₀₁ to R₂₀₄ may each independently be selected from a substituted orunsubstituted C₃-C₁₀ cycloalkyl group, a substituted or unsubstitutedC₁-C₁₀ heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀cycloalkenyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀ arylgroup, a substituted or unsubstituted C₆-C₆₀ aryloxy group, asubstituted or unsubstituted C₆-C₆₀ arylthio group, a substituted orunsubstituted C₁-C₆₀ heteroaryl group, a substituted or unsubstitutedmonovalent non-aromatic condensed polycyclic group, and a substituted orunsubstituted monovalent non-aromatic condensed heteropolycyclic group.

In some embodiments, in Formulae 201 and 202,

L₂₀₁ to L₂₀₅ may each independently be selected from

a phenylene group, a naphthylene group, a fluorenylene group, aspiro-fluorenylene group, a benzofluorene group, a dibenzofluorenegroup, a phenanthrenylene group, an anthracenylene group, a pyrenylenegroup, a chrysenylene group, a pyridinylene group, a pyrazinylene group,a pyrimidinylene group, a pyridazinylene group, a quinolinylene group,an isoquinolinylene group, a quinoxalinylene group, a quinazolinylenegroup, a carbazolylene group, and a triazinylene group; and

a phenylene group, a naphthylene group, a fluorenylene group, aspiro-fluorenylene group, a benzofluorene group, a dibenzofluorenegroup, a phenanthrenylene group, an anthracenylene group, a pyrenylenegroup, a chrysenylene group, a pyridinylene group, a pyrazinylene group,a pyrimidinylene group, a pyridazinylene group, a quinolinylene group,an isoquinolinylene group, a quinoxalinylene group, a quinazolinylenegroup, a carbazolylene group, and a triazinylene group, each substitutedwith at least one selected from a deuterium, —F, —Cl, —Br, —I, ahydroxyl group, a cyano group, a nitro group, an amino group, an amidinogroup, a hydrazine group, a hydrazone group, a carboxylic acid or a saltthereof, a sulfonic acid or a salt thereof, a phosphoric acid or a saltthereof, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a phenyl group, anaphthyl group, a fluorenyl group, a spiro-fluorenyl group, abenzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group,an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinylgroup, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, anisoindolyl group, a quinolinyl group, an isoquinolinyl group, aquinoxalinyl group, a quinazolinyl group, a carbazolyl group, and atriazinyl group;

xa1 to xa4 may each independently be 0, 1, or 2;

xa5 may be 1, 2, or 3;

R₂₀₁ to R₂₀₄ may each independently be selected from

a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenylgroup, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenylgroup, an anthracenyl group, a pyrenyl group, a chrysenyl group, apyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group,a quinazolinyl group, a carbazolyl group, and a triazinyl group; and

a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenylgroup, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenylgroup, an anthracenyl group, a pyrenyl group, a chrysenyl group, apyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group,a quinazolinyl group, a carbazolyl group, and a triazinyl group, eachsubstituted with at least one selected from a deuterium, —F, —Cl, —Br,—I, a hydroxyl group, a cyano group, a nitro group, an amino group, anamidino group, a hydrazine group, a hydrazone group, a carboxylic acidor a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acidor a salt thereof, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a phenylgroup, a naphthyl group, an azulenyl group, a fluorenyl group, aspiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group,a phenanthrenyl group, an anthracenyl group, a pyrenyl group, achrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinylgroup, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group,a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, and atriazinyl group, but they are not limited thereto.

The compound represented by Formula 201 may be represented by Formula201A:

For example, the compound represented by Formula 201 may be representedby Formula 201A-1 below:

For example, the compound represented by Formula 202 may be representedby Formula 202A below:

Descriptions of L₂₀₁ to L₂₀₃, xa1 to xa3, xa5, and R₂₀₂ to R₂₀₄ inFormulae 201A, 201A-1, and 202A are the same as described above, adescription of R₂11 is the same as defined in connection with R₂₀₃, andR₂₁₃ to R₂₁₆ may each independently be selected from a hydrogen, adeuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine group, a hydrazonegroup, a carboxylic acid group or a salt thereof, a sulfonic acid or asalt thereof, a phosphoric acid or a salt thereof, a C₁-C₆₀ alkyl group,a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, aC₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, aC₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀aryl group, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monvalent non-aromatic condensed polycyclic group,and a monvalent non-aromatic condensed heteropolycyclic group.

The compound represented by Formula 201, and the compound represented byFormula 202 may each include compounds HT1 to HT20 illustrated below.

A thickness of the hole transport region may be in a range of about 100Å to about 10000 Å, e.g., about 100 Å to about 1000 Å. When the holetransport region includes a hole injection layer and a hole transportlayer, the thickness of the hole injection layer may be in a range ofabout 100 Å to about 10000 Å, e.g., about 100 Å to about 1000 Å, and thethickness of the hole transport layer may be in a range of about 50 Å toabout 2000 Å, e.g., about 100 Å to about 1500 Å. When the thicknesses ofthe hole transport region, the hole injection layer, and the holetransport layer are within these ranges, satisfactory hole transportingcharacteristics may be obtained without a substantial increase indriving voltage.

The hole transport region may further include, in addition to thesematerials, a charge-generation material for the improvement ofconductive properties. The charge-generation material may behomogeneously or unhomogeneously dispersed in the hole transport region.

The charge-generation material may be, e.g., a p-dopant. The p-dopantmay be one selected from a quinone derivative, a metal oxide, and acyano group-containing compound. For example, non-limiting examples ofthe p-dopant are a quinone derivative, such astetracyanoquinonedimethane (TCNQ) or2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinonedimethane (F4-TCNQ); ametal oxide, such as a tungsten oxide or a molybdenum oxide, andCompound HT-D1 illustrated below.

The hole transport region may further include, in addition to the holeinjection layer and the hole transport layer, at least one of a bufferlayer and an electron blocking layer. Since the buffer layer maycompensate for an optical resonance distance according to a wavelengthof light emitted from the emission layer, light-emission efficiency of aformed organic light-emitting device may be improved. For use as amaterial included in the buffer layer, materials that are included inthe hole transport region may be used. The electron blocking layerprevents injection of electrons from the electron transport region.

For example, a material for the electron blocking layer may be mCP.

An emission layer may be formed on the first electrode 110 or the holetransport region by using various methods, e.g., vacuum deposition, spincoating, casting, a LB method, ink-jet printing, laser-printing, orlaser-induced thermal imaging. When the emission layer is formed byvacuum deposition or spin coating, deposition and coating conditions forthe emission layer may be determined by referring to the deposition andcoating conditions for the hole injection layer.

When the organic light-emitting device 10 is a full color organiclight-emitting device, the emission layer may be patterned into a redemission layer, a green emission layer, or a blue emission layer,according to a sub pixel. In some embodiments, the emission layer mayhave a stacked structure of a red emission layer, a green emissionlayer, and a blue emission layer, or may include a red-light emissionmaterial, a green-light emission material, and a blue-light emissionmaterial, which are mixed with each other in a single layer, to emitwhite light.

The emission layer may include the condensed cyclic compound representedby Formula 1.

The emission layer may include a host and a dopant. The dopant mayinclude the condensed cyclic compound represented by Formula 1.

The host may include, e.g., at least one selected from TPBi, TBADN, ADN(also referred to as “DNA”), CBP, CDBP, and TCP.

In some embodiments, the host may include a compound represented byFormula 301 below.Ar₃₀₁-[(L₃₀₁)_(xb1)-R₃₀₁]_(xb2)  <Formula 301>

In Formula 301,

Ar₃₀₁ may be selected from

a naphthalene, a heptalene, a fluorenene, a spiro-fluorenene, abenzofluorenene, a dibenzofluorenene, a phenalene, a phenanthrene, ananthracene, a fluoranthene, a triphenylene, a pyrene, a chrysene, anaphthacene, a picene, a perylene, a pentaphene, and anindenoanthracene;

a naphthalene, a heptalene, a fluorenene, a spiro-fluorenene, abenzofluorenene, a dibenzofluorenene, a phenalene, a phenanthrene, ananthracene, a fluoranthene, a triphenylene, a pyrene, a chrysene, anaphthacene, a picene, a perylene, a pentaphene, and anindenoanthracene, each substituted with at least one selected from adeuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine group, a hydrazonegroup, a carboxylic acid or a salt thereof, a sulfonic acid or a saltthereof, a phosphoric acid or a salt thereof, a C₁-C₆₀ alkyl group, aC₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy, a C₃-C₁₀cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenylgroup, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀aryloxy, a C₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, amonovalent non-aromatic condensed polycyclic group, a monovalentnon-aromatic condensed heteropolycyclic group, and —Si(Q₃₀₁)(Q₃₀₂)(Q₃₀₃)(wherein Q₃₀₁ to Q₃₀₃ are each independently selected from a hydrogen, aC₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₁-C₆₀ aryl group, and aC₁-C₆₀ heteroaryl group);

L₃₀₁ may be the same as explained in connection with L₁;

R₃₀₁ may be selected from

a C₁-C₂₀ alkyl group and a C₁-C₂₀ alkoxy group;

a C₁-C₂₀ alkyl group and a C₁-C₂₀ alkoxy group, each substituted with atleast one selected from a deuterium, —F, —Cl, —Br, —I, a hydroxyl group,a cyano group, a nitro group, an amino group, an amidino group, ahydrazine group, a hydrazone group, a carboxylic acid or a salt thereof,a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof,a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenylgroup, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenylgroup, an anthracenyl group, a pyrenyl group, a chrysenyl group, apyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group,a quinazolinyl group, a carbazolyl group, and a triazinyl group;

a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenylgroup, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenylgroup, an anthracenyl group, a pyrenyl group, a chrysenyl group, apyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group,a quinazolinyl group, a carbazol group, and a triazinyl group; and

a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenylgroup, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenylgroup, an anthracenyl group, a pyrenyl group, a chrysenyl group, apyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group,a quinazolinyl group, a carbazolyl group and a triazinyl group, eachsubstituted with at least one selected from a deuterium, —F, —Cl, —Br,—I, a hydroxyl group, a cyano group, a nitro group, an amino group, anamidino group, a hydrazine group, a hydrazone group, a carboxylic acidor a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acidor a salt thereof, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a phenylgroup, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, abenzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group,an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinylgroup, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, aquinolinyl group, an isoquinolinyl group, a quinoxalinyl group, aquinazolinyl group, a carbazolyl group, and a triazinyl group;

xb1 may be selected from 0, 1, 2, and 3;

xb2 may be selected from 1, 2, 3, and 4.

wherein in Formula 301,

L₃₀₁ may be selected from

a phenylene group, a naphthylene group, a fluorenylene group, aspiro-fluorenylene group, a benzofluorenylene group, adibenzofluorenylene group, a phenanthrenylene group, an anthracenylenegroup, a pyrenylene group, and a chrysenylene group; and

a phenylene group, a naphthylene group, a fluorenylene group, aspiro-fluorenylene group, a benzofluorenylene group, adibenzofluorenylene group, a phenanthrenylene group, an anthracenylenegroup, a pyrenylene group, and a chrysenylene group, each substitutedwith at least one selected from a deuterium, —F, —Cl, —Br, —I, ahydroxyl group, a cyano group, a nitro group, an amino group, an amidinogroup, a hydrazine group, a hydrazone group, a carboxylic acid or a saltthereof, a sulfonic acid or a salt thereof, a phosphoric acid or a saltthereof, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a phenyl group, anaphthyl group, a fluorenyl group, a spiro-fluorenyl group, abenzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group,an anthracenyl group, a pyrenyl group, and a chrysenyl group;

R₃₀₁ may be selected from

a C₁-C₂₀ alkyl group and a C₁-C₂₀ alkoxy group;

a C₁-C₂₀ alkyl group and a C₁-C₂₀ alkoxy group, each substituted with atleast one selected from a deuterium, —F, —Cl, —Br, —I, a hydroxyl group,a cyano group, a nitro group, an amino group, an amidino group, ahydrazine group, a hydrazone group, a carboxylic acid or a salt thereof,a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof,a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenylgroup, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenylgroup, an anthracenyl group, a pyrenyl group, and a chrysenyl group;

a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenylgroup, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenylgroup, an anthracenyl group, a pyrenyl group, and a chrysenyl group; and

a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenylgroup, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenylgroup, an anthracenyl group, a pyrenyl group, and a chrysenyl group,each substituted with at least one selected from a deuterium, —F, —Cl,—Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group,an amidino group, a hydrazine group, a hydrazone group, a carboxylicacid or a salt thereof, a sulfonic acid or a salt thereof, a phosphoricacid or a salt thereof, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, aphenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenylgroup, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenylgroup, an anthracenyl group, a pyrenyl group, and a chrysenyl group, butis not limited thereto.

For example, the host may include a compound represented by Formula 301Abelow.

Descriptions of substituents of Formula 301A may be understood byreferring to the descriptions provided herein.

The compound represented by Formula 301 may include at least one ofCompounds H1 to H42.

In some embodiments, the host may include at least one of Compounds H43to H49 below.

The dopant may include at least one selected from a fluorescent dopantand a phosphorescent dopant. When the dopant includes a fluorescentdopant, the fluorescent dopant may include the condensed cyclic compoundrepresented by Formula 1.

The fluorescent dopant may include, in addition to the condensed cycliccompound represented by Formula 1, at least one selected from DPAVBi,BDAVBi, TBPe, DCM, DCJTB, Coumarin 6, and C545T.

An amount of the dopant in the emission layer may be, e.g., in a rangeof about 0.01 to about 15 parts by weight based on 100 parts by weightof the host.

A thickness of the emission layer may be in a range of about 100 Å toabout 1000 Å, for example, about 200 Å to about 600 Å. When thethickness of the emission layer is within this range, excellentlight-emission characteristics may be obtained without a substantialincrease in driving voltage.

Then, an electron transport region may be disposed on the emissionlayer.

The electron transport region may include at least one selected from ahole blocking layer, an electron transport layer (ETL), and an electroninjection layer.

For example, the electron transport region may have a structure ofelectron transport layer/electron injection layer or a structure of holeblocking layer/electron transport layer/electron injection layer,wherein layers of each structure are sequentially stacked from theemission layer in the stated order, but is not limited thereto.

According to an embodiment, the organic layer 150 of the organiclight-emitting device may include an electron transport region disposedbetween the emission layer and the second electrode 190.

When the electron transport region includes a hole blocking layer, thehole blocking layer may be formed on the emission layer by using variousmethods, such as vacuum deposition, spin coating casting, a LB method,ink-jet printing, laser-printing, or laser-induced thermal imaging. Whenthe hole blocking layer is formed by vacuum deposition or spin coating,deposition and coating conditions for the hole blocking layer may bedetermined by referring to the deposition and coating conditions for thehole injection layer.

The hole blocking layer may include, e.g., at least one of BCP andBphen.

A thickness of the hole blocking layer may be in a range of about 20 Åto about 1000 Å, e.g., about 30 Å to about 300 Å. When the thickness ofthe hole blocking layer is within these ranges, the hole blocking layermay have improved hole blocking ability without a substantial increasein driving voltage.

The electron transport region may include an electron transport layer.The electron transport layer may be formed on the emission layer or thehole blocking layer by using various methods, such as vacuum deposition,spin coating casting, a LB method, ink-jet printing, laser-printing, orlaser-induced thermal imaging. When an electron transport layer isformed by vacuum deposition or spin coating, deposition and coatingconditions for the electron transport layer may be determined byreferring to the deposition and coating conditions for the holeinjection layer.

In some embodiments, the electron transport layer may include at leastone compound selected from a compound represented by Formula 601 and acompound represented by Formula 602 illustrated below.Ar₆₀₁-[(L₆₀₁)_(xe1)-E₆₀₁]_(xe2)  <Formula 601>

In Formula 601,

Ar₆₀₁ may be selected from:

a naphthalene, a heptalene, a fluorenene, a spiro-fluorenene, abenzofluorenene, a dibenzofluorenene, a phenalene, a phenanthrene, ananthracene, a fluoranthene, a triphenylene, a pyrene, a chrysene, anaphthacene, a picene, a perylene, a pentaphene, and anindenoanthracene;

a naphthalene, a heptalene, a fluorenene, a spiro-fluorenene, abenzofluorenene, a dibenzofluorenene, a phenalene, a phenanthrene, ananthracene, a fluoranthene, a triphenylene, a pyrene, a chrysene, anaphthacene, a picene, a perylene, a pentaphene, and anindenoanthracene, each substituted with at least one selected from adeuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine group, a hydrazonegroup, a carboxylic acid group or a salt thereof, a sulfonic acid or asalt thereof, a phosphoric acid or a salt thereof, a C₁-C₆₀ alkyl group,a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy, aC₃-C₁₀cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, aC₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀aryl group, a C₆-C₆₀ aryloxy, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,a monovalent non-aromatic condensed heteropolycyclic group, and—Si(Q₃₀₁)(Q₃₀₂)(Q₃₀₃) (wherein Q₃₀₁ to Q₃₀₃ are each independently ahydrogen, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₆-C₆₀ arylgroup, or a C₁-C₆₀ heteroaryl group);

L₆₀₁ may be the same as explained in connection with L₂₀₁;

E₆₀₁ may be selected from:

a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolylgroup, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, anoxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinylgroup, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, anindolyl group, an indazolyl group, a purinyl group, a quinolinyl group,an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, anaphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, acinnolinyl group, a carbazolyl group, a phenanthridinyl group, anacridinyl group, a phenanthrolinyl group, a phenazinyl group, abenzoimidazolyl group, a benzofuranyl group, a benzothiophenyl group, anisobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group,a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinylgroup, a dibenzofuranyl group, a dibenzothiophenyl group, abenzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinylgroup, and an imidazopyrimidinyl group; and

a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolylgroup, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, anoxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinylgroup, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, anindolyl group, an indazolyl group, a purinyl group, a quinolinyl group,an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, anaphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, acinnolinyl group, a carbazolyl group, a phenanthridinyl group, anacridinyl group, a phenanthrolinyl group, a phenazinyl group, abenzoimidazolyl group, a benzofuranyl group, a benzothiophenyl group, anisobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group,a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinylgroup, a dibenzofuranyl group, a dibenzothiophenyl group, abenzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinylgroup, and an imidazopyrimidinyl group, each substituted with at leastone selected from a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, acyano group, a nitro group, an amino group, an amidino group, ahydrazine group, a hydrazone group, a carboxylic acid or a salt thereof,a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof,a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a phenyl group, apentalenyl group, an indenyl group, a naphthyl group, an azulenyl group,a heptalenyl group, an indacenyl group, an acenaphthyl group, afluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, ananthracenyl group, a fluoranthenyl group, a triphenylenyl group, apyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group,a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenylgroup, a rubicenyl group, a coronenyl group, an ovalenyl group, apyrrolyl group, a thiophenyl group, a furanyl group, an imidazolylgroup, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, anoxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinylgroup, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, anindolyl group, an indazolyl group, a purinyl group, a quinolinyl group,an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, anaphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, acinnolinyl group, a carbazolyl group, a phenanthridinyl group, anacridinyl group, a phenanthrolinyl group, a phenazinyl group, abenzoimidazolyl group, a benzofuranyl group, a benzothiophenyl group, anisobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group,a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinylgroup, a dibenzofuranyl group, a dibenzothiophenyl group, abenzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinylgroup, and an imidazopyrimidinyl group;

xe1 may be selected from 0, 1, 2, and 3; and

xe2 may be selected from 1, 2, 3, and 4.

In Formula 602,

X₆₁₁ may be N or C-(L₆₁₁)_(xe611)-R₆₁₁, X₆₁₂ may be N orC-(L₆₁₂)_(xe612)-R₆₁₂, X₆₁₃ may be N or C-(L₆₁₃)_(xe613)-R₆₁₃ and, atleast one of X₆₁₁ to X₆₁₃ may be N;

L₁₁ to L₆₁₆ may be the same as explained in connection with L₁;

R₆₁₁ to R₆₁₆ may each independently be selected from

a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenylgroup, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenylgroup, an anthracenyl group, a pyrenyl group, a chrysenyl group, apyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group,a quinazolinyl group, a carbazolyl group, and a triazinyl group; and

a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenylgroup, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenylgroup, an anthracenyl group, a pyrenyl group, a chrysenyl group, apyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group,a quinazolinyl group, a carbazolyl group, and a triazinyl group, eachsubstituted with at least one selected from a deuterium, —F, —Cl, —Br,—I, a hydroxyl group, a cyano group, a nitro group, an amino group, anamidino group, a hydrazine group, a hydrazone group, a carboxylic acidor a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acidor a salt thereof, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a phenylgroup, a naphthyl group, an azulenyl group, a fluorenyl group, aspiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group,a phenanthrenyl group, an anthracenyl group, a pyrenyl group, achrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinylgroup, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group,a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, and atriazinyl group;

xe611 to xe616 may each independently be selected from 0, 1, 2, and 3.

The compound represented by Formula 601 and the compound represented byFormula 602 may each independently be selected from Compounds ET1 toET15 illustrated below:

In some embodiments, the electron transport layer may further include atleast one selected from BCP, Bphen, Alq₃, Balq, TAZ, and NTAZ.

A thickness of the electron transport layer may be in a range of about100 Å to about 1000 Å, e.g., about 150 Å to about 500 Å. When thethickness of the electron transport layer is within the range describedabove, the electron transport layer may have satisfactory electrontransport characteristics without a substantial increase in drivingvoltage.

In an implementation, the electron transport layer may further include,in addition to the materials described above, a metal-containingmaterial.

The metal-containing material may include a Li complex. The Li complexmay include, e.g., Compound ET-D1 (lithium quinolate, LiQ) or ET-D2.

The electron transport region may include an electron injection layerthat facilitates electron injection from the second electrode 190.

The electron injection layer may be formed on the electron transportlayer by using various methods, such as vacuum deposition, spin coatingcasting, a LB method, ink-jet printing, laser-printing, or laser-inducedthermal imaging. When an electron injection layer is formed by vacuumdeposition or spin coating, deposition and coating conditions for theelectron injection layer may be determined by referring to thedeposition and coating conditions for the hole injection layer.

The electron injection layer may include at least one selected from,LiF, NaCl, CsF, Li₂O, BaO, and LiQ.

A thickness of the electron injection layer may be in a range of about 1Å to about 100 Å, e.g., about 3 Å to about 90 Å. When the thickness ofthe electron injection layer is within the range described above, theelectron injection layer may have satisfactory electron injectioncharacteristics without a substantial increase in driving voltage.

The second electrode 190 may be disposed on the organic layer 150 havingsuch a structure. The second electrode 190 may be a cathode that is anelectron injection electrode, and in this regard, a material for formingthe second electrode 190 may be a material having a low work function,and such a material may include metal, alloy, an electrically conductivecompound, or a mixture thereof. Examples of the material for the secondelectrode 190 may include lithium (Li), magnesium (Mg), aluminum (Al),aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), ormagnesium-silver (Mg—Ag). In some embodiments, the material for formingthe second electrode 190 may be ITO or IZO. The second electrode 190 maybe a semi-transmissive electrode or a transmissive electrode.

Hereinbefore, the organic light-emitting device has been described withreference to FIG. 1.

A C₁-C₆₀ alkyl group used herein refers to a linear or branchedaliphatic hydrocarbon monovalent group having 1 to 60 carbon atoms, anddetailed examples thereof are a methyl group, an ethyl group, a propylgroup, an isobutyl group, a sec-butyl group, a ter-butyl group, a pentylgroup, an iso-amyl group, and a hexyl group. A C₁-C₆₀ alkylene groupused herein refers to a divalent group having the same structure as theC₁-C₆₀ alkyl group.

A C₁-C₆₀ alkoxy group used herein refers to a monovalent grouprepresented by —OA₁₀₁ (wherein A₁₀₁ is the C₁-C₆₀ alkyl group), anddetailed examples thereof are a methoxy group, an ethoxy group, and anisopropyloxy group.

A C₂-C₆₀ alkenyl group used herein refers to a hydrocarbon group formedby substituting at least one carbon double bond in the middle or at theterminal of the C₂-C₆₀ alkyl group, and detailed examples thereof are anethenyl group, a prophenyl group, and a butenyl group. A C₂-C₆₀ alkylenegroup used herein refers to a divalent group having the same structureas the C₂-C₆₀ alkyl group.

A C₂-C₆₀ alkynyl group used herein refers to a hydrocarbon group formedby substituting at least one carbon trip bond in the middle or at theterminal of the C₂-C₆₀ alkyl group, and detailed examples thereof are anethynyl group, and a propynyl group. A C₂-C₆₀ alkylene group used hereinrefers to a divalent group having the same structure as the C₂-C₆₀ alkylgroup.

A C₃-C₁₀ cycloalkyl group used herein refers to a monovalent hydrocarbonmonocyclic group having 3 to 10 carbon atoms, and detailed examplesthereof are a cyclopropyl group, a cyclobutyl group, a cyclopentylgroup, a cyclohexyl group, and a cycloheptyl group. A C₃-C₁₀cycloalkylene group used herein refers to a divalent group having thesame structure as the C₃-C₁₀ cycloalkyl group.

A C₁-C₁₀ heterocycloalkyl group used herein refers to a monovalentmonocyclic group having at least one hetero atom selected from N, O, Si,P, and S as a ring-forming atom and 1 to 10 carbon atoms, and detailedexamples thereof are a tetrahydrofuranyl group, and atetrahydrothiophenyl group. A C₁-C₁₀ heterocycloalkylene group usedherein refers to a divalent group having the same structure as theC₁-C₁₀ heterocycloalkyl group.

A C₃-C₁₀ cycloalkenyl group used herein refers to a monovalentmonocyclic group that has 3 to 10 carbon atoms and at least one doublebond in the ring thereof and does not have aromacity, and detailedexamples thereof are a cyclopentenyl group, a cyclohexenyl group, and acycloheptenyl group. A C₃-C₁₀ cycloalkenylene group used herein refersto a divalent group having the same structure as the C₃-C₁₀ cycloalkenylgroup.

A C₁-C₁₀ heterocycloalkenyl group used herein refers to a monovalentmonocyclic group that has at least one hetero atom selected from N, O,Si, P, and S as a ring-forming atom, 1 to 10 carbon atoms, and at leastone double bond in its ring. Detailed examples of the C₁-C₁₀heterocycloalkenyl group are a 2,3-hydrofuranyl group and a2,3-hydrothiophenyl group. A C₁-C₁₀ heterocycloalkenylene group usedherein refers to a divalent group having the same structure as theC₁-C₁₀ heterocycloalkenyl group.

A C₆-C₆₀ aryl group used herein refers to a monovalent group having acarbocyclic aromatic system having 6 to 60 carbon atoms, and a C₆-C₆₀arylene group used herein refers to a divalent group having acarbocyclic aromatic system having 6 to 60 carbon atoms. Detailedexamples of the C₆-C₆₀ aryl group are a phenyl group, a naphthyl group,an anthracenyl group, a phenanthrenyl group, a pyrenyl group, and achrysenyl group. When the C₆-C₆₀ aryl group and the C₆-C₆₀ arylene groupeach include two or more rings, the rings may be fused to each other.

A C₁-C₆₀ heteroaryl group used herein refers to a monovalent grouphaving a carbocyclic aromatic system that has at least one hetero atomselected from N, O, Si, P, and S as a ring-forming atom, and 1 to 60carbon atoms. A C₁-C₆₀ heteroarylene group used herein refers to adivalent group having a carbocyclic aromatic system that has at leastone hetero atom selected from N, O, P, and S as a ring-forming atom, and1 to 60 carbon atoms. Examples of the C₁-C₆₀ heteroaryl group are apyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinylgroup, a triazinyl group, a quinolinyl group, and an isoquinolinylgroup. When the C₁-C₆₀ heteroaryl group and the C₁-C₆₀ heteroarylenegroup each include two or more rings, the rings may be fused to eachother.

A C₆-C₆₀ aryloxy group used herein indicates —OA₁₀₂ (wherein A₁₀₂ is theC₆-C₆₀ aryl group), and a C₆-C₆₀ arylthio group used herein indicates—SA₁₀₃ (wherein A₁₀₃ is the C₆-C₆₀ aryl group).

A monovalent non-aromatic condensed polycyclic group used herein refersto a monovalent group (for example, having 8 to 60 carbon atoms) thathas two or more rings condensed to each other, only carbon atoms as aring forming atom, and non-aromacity in the entire molecular structure.A detailed example of the monovalent non-aromatic condensed polycyclicgroup is a fluorenyl group. A divalent non-aromatic condensed polycyclicgroup used herein refers to a divalent group having the same structureas the monovalent non-aromatic condensed polycyclic group.

A monovalent non-aromatic condensed heteropolycyclic group used hereinrefers to a monovalent group (for example, having 2 to 60 carbon atoms)that has two or more rings condensed to each other, has a heteroatomselected from N, O, Si, P, and S, other than carbon atoms, as a ringforming atom, and has non-aromacity in the entire molecular structure.An example of the monovalent non-aromatic condensed heteropolycyclicgroup is a carbazolyl group. A divalent non-aromatic condensedheteropolycyclic group used herein refers to a divalent group having thesame structure as the monovalent non-aromatic condensed heteropolycyclicgroup.

at least one of substituents of the substituted C₃-C₁₀ cycloalkylenegroup, substituted C₁-C₁₀ heterocycloalkylene group, substituted C₃-C₁₀cycloalkenylene group, substituted C₁-C₁₀ heterocycloalkenylene group,substituted C₆-C₆₀ arylene group, substituted C₁-C₆₀ heteroarylenegroup, substituted divalent non-aromatic condensed polycyclic group,substituted divalent non-aromatic condensed heteropolycyclic group,substituted C₁-C₆₀ alkyl group, substituted C₂-C₆₀ alkenyl group,substituted C₂-C₆₀ alkynyl group, substituted C₁-C₆₀ alkoxy group,substituted C₃-C₁₀ cycloalkyl group, substituted C₁-C₁₀ heterocycloalkylgroup, substituted C₃-C₁₀ cycloalkenyl group, substituted C₁-C₁₀heterocycloalkenyl group, substituted C₆-C₆₀ aryl group, substitutedC₆-C₆₀ aryloxy group, substituted C₆-C₆₀ arylthio group, substitutedC₁-C₆₀ heteroaryl group, substituted monovalent non-aromatic condensedpolycyclic group, and substituted monovalent non-aromatic condensedheteropolycyclic group may be selected from

a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine group, a hydrazonegroup, a carboxylic acid or a salt thereof, a sulfonic acid or a saltthereof, a phosphoric acid or a salt thereof, a C₁-C₆₀ alkyl group, aC₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, and a C₁-C₆₀ alkoxy group;

a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group,and a C₁-C₆₀ alkoxy group, each substituted with at least one selectedfrom a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, anitro group, an amino group, an amidino group, a hydrazine group, ahydrazone group, a carboxylic acid group or a salt thereof, a sulfonicacid group or a salt thereof, a phosphoric acid group or a salt thereof,a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,a monovalent non-aromatic condensed heteropolycyclic group, and—Si(Q₁₁)(Q₁₂)(Q₁₃);

a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,and a monovalent non-aromatic heterocondensed polycyclic group;

a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,and a monovalent non-aromatic heterocondensed polycyclic group, eachsubstituted with at least one selected from a deuterium, —F, —Cl, —Br,—I, a hydroxyl group, a cyano group, a nitro group, an amino group, anamidino group, a hydrazine group, a hydrazone group, a carboxylic acidgroup or a salt thereof, a sulfonic acid group or a salt thereof, aphosphoric acid group or a salt thereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenylgroup, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, amonovalent non-aromatic condensed polycyclic group, a monovalentnon-aromatic heterocondensed polycyclic group, —Si(Q₂₁)(Q₂₂)(Q₂₃), and—B(Q₂₄)(Q₂₅); and

—Si(Q₃₁)(Q₃₂)(Q₃₃),

wherein Q₁ to Q₃, Q₁₁ to Q₃, Q₂₁ to Q₂₃, and Q₃₁ to Q₃₃ may be eachindependently selected from a hydrogen, a deuterium, —F, —Cl, —Br, —I, ahydroxyl group, a cyano group, a nitro group, an amino group, an amidinogroup, a hydrazine group, a hydrazone group, a carboxylic acid or a saltthereof, a sulfonic acid or a salt thereof, a phosphoric acid or a saltthereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynylgroup, a C₁-C₆₀ alkoxy group, a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₁-C₆₀ heteroarylgroup, a monovalent non-aromatic condensed polycyclic group, and amonovalent non-aromatic condensed heteropolycyclic group.

The term “Ph” used herein refers to a phenyl group, the term “Me” usedherein refers to a methyl group, the term “Et” used herein refers to anethyl group, and the term “ter-Bu” or “Bu^(t)” used herein refers to atert-butyl group.

Hereinafter, an organic light-emitting device according to an embodimentwill be described in detail with reference to Synthesis Examples andExamples. The wording “B was used instead of A” used in describingSynthesis Examples means that a molar equivalent of A was identical to amolar equivalent of B.

The following Examples and Comparative Examples are provided in order tohighlight characteristics of one or more embodiments, but it will beunderstood that the Examples and Comparative Examples are not to beconstrued as limiting the scope of the embodiments, nor are theComparative Examples to be construed as being outside the scope of theembodiments. Further, it will be understood that the embodiments are notlimited to the particular details described in the Examples andComparative Examples.

EXAMPLE Synthesis Example 1 Synthesis of Compound 1

Synthesis of Intermediate A-1

6,12-dibromochrysene (38.6 g, 100 mmol) was dissolved in 1.5 L ofo-xylene and then the result was heated. When 6,12-dibromochrysene wascompletely dissolved, PdPPh₄ (2.3 g, 5 mmol), K₃PO₄ (42.4 g, 200 mmol),and (4-chloro-2-methoxyphenyl)boronic acid (22.4 g, 120 mmol) were addedthereto, and the resultant mixture was reflux-stirred for 1 hour at atemperature of 140° C. When the temperature was dropped to ambienttemperature, an extraction process was performed thereon by usingmethylenechloride (MC). Column chromatography was performed thereon toobtain Intermediate A-1 (24.6 g, 55 mmol, yield of 55%).

Synthesis of Intermediate A-2

Intermediate A-1 (24.6 g, 55 mmol) was dissolved in 1.5 L of THF, andthen, the result was cooled to a temperature of −78° C. n-BuLi wasslowly added thereto, and then stirred for 1 hour. Fluorodiphenylborane(11.0 g, 60 mmol) dissolved in 300 ml of tetrahydrofuran (THF) was addedto the mixture, and then, slowly heated to ambient temperature, theresultant solution was stirred for 12 hours. Once the reaction wascomplete, the resultant solution was neutralized by using a HCl aqueoussolution until a pH thereof reached 5. Subsequently, a solvent wasevaporated therefrom and an extraction process was performed thereon byusing MC. A column chromatography was performed thereon to obtainIntermediate A-2 (20.5 g, 38 mmol, yield of 70%).

Synthesis of Intermediate A-3

Intermediate A-2 (10.6 g, 15 mmol), diphenylamine (3.0 g, 18 mmol),tris(dibenzylideneacetone)dipalladium(0) (275 mg, 0.3 mmol),tri(tert-butyl)phosphine (121 mg, 0.6 mmol), and sodium tert-butoxide(2.9 mg, 30 mmol) were dissolved in 50 ml of toluene, and then, themixture was stirred at a temperature of 80° C. for 2 hours. Thetemperature was dropped to ambient temperature, and then an extractionprocess was performed thereon using ethyl acetate. Column chromatographywas performed thereon to obtain Intermediate A-3 (8.0 g, 12 mmol, yield80%).

Synthesis of Intermediate A-4

Intermediate A-3 (8.0 g, 12 mmol) and sodium ethanethiolate (2.0 g, 24mmol) were dissolved in 100 mL of DMF, and then, the result wasreflux-stirred at a temperature of 150° C. for 4 hours. The temperaturewas dropped to ambient temperature, and then an extraction process wasperformed thereon using ethyl acetate. Column chromatography wasperformed thereon to obtain Intermediate A-4 (5.4 g, 8.4 mmol, yield of70%).

Synthesis of Compound 1

Intermediate A-4 (5.4 g, 8.4 mmol) and Cu₂O (6.0 g, 42 mmol) weredissolved in 50 mL of nitrobenzene, and then, the result wasreflux-stirred at a temperature of 180° C. for 12 hours. The temperaturewas dropped to ambient temperature, and then an extraction process wasperformed thereon using ethyl acetate. Column chromatography wasperformed thereon to obtain Compound 1 (4.9 g, 7.6 mmol, yield of 90%).

Synthesis Example 2 Synthesis of Compound 4

Synthesis of Intermediate A-1

6,12-dibromochrysene (38.6 g, 100 mmol) was dissolved in 1.5 L ofo-xylene and then the result was heated. When 6,12-dibromochrysene wascompletely dissolved, PdPPh₄ (2.3 g, 5 mmol), K₃PO₄ (42.4 g, 200 mmol),and (4-chloro-2-methoxyphenyl)boronic acid (22.4 g, 120 mmol) were addedthereto, and the resultant mixture was reflux-stirred for 1 hour at atemperature of 140° C. When the temperature was dropped to ambienttemperature, an extraction process was performed thereon using methylenechloride (MC). Column chromatography was performed thereon to obtainIntermediate A-1 (24.6 g, 55 mmol, yield of 55%).

Synthesis of Intermediate A-6

Intermediate A-6 was obtained in a yield of 70% in the same manner asused to synthesize Intermediate A-2, except that(2,4-dimethylphenyl)(3,5-dimethylphenyl)fluoroborane was used instead offluorodiphenylborane.

Synthesis of Intermediate A-7

Intermediate A-7 was obtained in a yield of 83% in the same manner asused to synthesize Intermediate A-3, except that Intermediate A-6 wasused instead of Intermediate A-2 and N-phenylnaphthalen-2-amine was usedinstead of diphenylamine.

Synthesis of Intermediate A-8

Intermediate A-8 was obtained in a yield of 70% in the same manner asused to synthesize Intermediate A-4, except that Intermediate A-7 wasused instead of Intermediate A-3.

Synthesis of Compound 4

Compound 4 was obtained in a yield of 85% in the same manner as used tosynthesize Compound 1, except that Intermediate A-8 was used instead ofIntermediate A-4.

Synthesis Example 3 Synthesis of Compound 14

Synthesis of Intermediate A-1

6,12-dibromochrysene (38.6 g, 100 mmol) was dissolved in 1.5 L ofo-xylene and then the result was heated. When 6,12-dibromochrysene wascompletely dissolved, PdPPh₄ (2.3 g, 5 mmol), K₃PO₄ (42.4 g, 200 mmol),and (4-chloro-2-methoxyphenyl)boronic acid (22.4 g, 120 mmol) were addedthereto, and the resultant mixture was reflux-stirred for 1 hour at atemperature of 140° C. When the temperature was dropped to ambienttemperature, an extraction process was performed thereon using methylenechloride (MC). Column chromatography was performed thereon to obtainIntermediate A-1 (24.6 g, 55 mmol, yield of 55%).

Synthesis of Intermediate A-9

Intermediate A-9 was obtained in a yield of 72% in the same manner asused to synthesize Intermediate A-2, except that[1,1′-biphenyl]-2-yl(9,9-dimethyl-9H-fluoren-3-yl)fluoroborane was usedinstead of fluorodiphenylborane.

Synthesis of Intermediate A-10

Intermediate A-10 was obtained in a yield of 79% in the same manner asused to synthesize Intermediate A-3, except that Intermediate A-9 wasused instead of Intermediate A-2 and([1,1′-biphenyl]-2-yl)-9,9-dimethyl-9H-fluoren-3-amine was used insteadof diphenylamine.

Synthesis of Intermediate A-11

Intermediate A-11 was obtained in a yield of 73% in the same manner asused to synthesize Intermediate A-4, except that Intermediate A-10 wasused instead of Intermediate A-3.

Synthesis of Compound 14

Compound 14 was obtained in a yield of 80% in the same manner as used tosynthesize Compound 1, except that Intermediate A-11 was used instead ofIntermediate A-4.

Synthesis Example 4 Synthesis of Compound 22

Synthesis of Intermediate A-1

6,12-dibromochrysene (38.6 g, 100 mmol) was dissolved in 1.5 L ofo-xylene and then the result was heated. When 6,12-dibromochrysene wascompletely dissolved, PdPPh₄ (2.3 g, 5 mmol), K₃PO₄ (42.4 g, 200 mmol),and (4-chloro-2-methoxyphenyl)boronic acid (22.4 g, 120 mmol) were addedthereto, and the resultant mixture was reflux-stirred for 1 hour at atemperature of 140° C. When the temperature was dropped to ambienttemperature, an extraction process was performed thereon using methylenechloride (MC). Column chromatography was performed thereon to obtainIntermediate A-1 (24.6 g, 55 mmol, yield of 55%).

Synthesis of Intermediate A-12

Intermediate A-12 was obtained in a yield of 75% in the same manner asused to synthesize Intermediate A-2, except that[1,1′-biphenyl]-2-ylfluoro(phenyl)borane was used instead offluorodiphenylborane.

Synthesis of Intermediate A-13

Intermediate A-13 was obtained in a yield of 81% in the same manner asused to synthesize Intermediate A-3, except that Intermediate A-12 wasused instead of Intermediate A-2 and 2,6-dimethyl-N-phenylaniline wasused instead of diphenylamine.

Synthesis of Intermediate A-14

Intermediate A-14 was obtained in a yield of 77% in the same manner asused to synthesize Intermediate A-4, except that Intermediate A-13 wasused instead of Intermediate A-3.

Synthesis of Compound 22

Compound 22 was obtained in a yield of 88% in the same manner as used tosynthesize Compound 1, except that Intermediate A-14 was used instead ofIntermediate A-4.

Synthesis Example 5 Synthesis of Compound 25

Synthesis of Intermediate A-1

6,12-dibromochrysene (38.6 g, 100 mmol) was dissolved in 1.5 L ofo-xylene and then the result was heated. When 6,12-dibromochrysene wascompletely dissolved, PdPPh₄ (2.3 g, 5 mmol), K₃PO₄ (42.4 g, 200 mmol),and (4-chloro-2-methoxyphenyl)boronic acid (22.4 g, 120 mmol) were addedthereto, and the resultant mixture was reflux-stirred for 1 hour at atemperature of 140° C. When the temperature was dropped to ambienttemperature, an extraction process was performed thereon using methylenechloride (MC). Column chromatography was performed thereon to obtainIntermediate A-1 (24.6 g, 55 mmol, yield of 55%).

Synthesis of Intermediate A-15

Intermediate A-15 was obtained in a yield of 80% in the same manner asused to synthesize Intermediate A-2, except thatfluoro(naphthalen-2-yl)(phenyl)borane was used instead offluorodiphenylborane.

Synthesis of Intermediate A-16

Intermediate A-16 was obtained in a yield of 88% in the same manner asused to synthesize Intermediate A-3, except that Intermediate A-12 wasused instead of Intermediate A-2.

Synthesis of Intermediate A-17

Intermediate A-17 was obtained in a yield of 81% in the same manner asused to synthesize Intermediate A-4, except that Intermediate A-16 wasused instead of Intermediate A-3.

Synthesis of Compound 25

Compound 25 was obtained in a yield of 87% in the same manner as used tosynthesize Compound 1, except that Intermediate A-17 was used instead ofIntermediate A-4.

Synthesis Example 6 Synthesis of Compound 33

Synthesis of Intermediate A-1

6,12-dibromochrysene (38.6 g, 100 mmol) was dissolved in 1.5 L ofo-xylene and then the result was heated. When 6,12-dibromochrysene wascompletely dissolved, PdPPh₄ (2.3 g, 5 mmol), K₃PO₄ (42.4 g, 200 mmol),and (4-chloro-2-methoxyphenyl)boronic acid (22.4 g, 120 mmol) were addedthereto, and the resultant mixture was reflux-stirred for 1 hour at atemperature of 140° C. When the temperature was dropped to ambienttemperature, an extraction process was performed thereon using methylenechloride (MC). Column chromatography was performed thereon to obtainIntermediate A-1 (24.6 g, 55 mmol, yield of 55%).

Synthesis of Intermediate A-18

Intermediate A-18 was obtained in a yield of 75% in the same manner asused to synthesize Intermediate A-2, except that fluorodimesitylboranewas used instead of fluorodiphenylborane.

Synthesis of Intermediate A-19

Intermediate A-19 was obtained in a yield of 79% in the same manner asused to synthesize Intermediate A-3, except that Intermediate A-18 wasused instead of Intermediate A-2 andN-([1,1′-biphenyl]-2-yl)-9,9-dimethyl-9H-fluoren-3-amine was usedinstead of diphenylamine.

Synthesis of Intermediate A-20

Intermediate A-20 was obtained in a yield of 75% in the same manner asused to synthesize Intermediate A-4, except that Intermediate A-19 wasused instead of Intermediate A-3.

Synthesis of Compound 33

Compound 33 was obtained in a yield of 83% in the same manner as used tosynthesize Compound 1, except that Intermediate A-20 was used instead ofIntermediate A-4.

Synthesis Example 7 Synthesis of Compound 46

Synthesis of Intermediate A-1

6,12-dibromochrysene (38.6 g, 100 mmol) was dissolved in 1.5 L ofo-xylene and then the result was heated. When 6,12-dibromochrysene wascompletely dissolved, PdPPh₄(2.3 g, 5 mmol), K₃PO₄ (42.4 g, 200 mmol),and (4-chloro-2-methoxyphenyl)boronic acid (22.4 g, 120 mmol) were addedthereto, and the resultant mixture was reflux-stirred for 1 hour at atemperature of 140° C. When the temperature was dropped to ambienttemperature, an extraction process was performed thereon using methylenechloride (MC). Column chromatography was performed thereon to obtainIntermediate A-1 (24.6 g, 55 mmol, yield of 55%).

Synthesis of Intermediate A-21

Intermediate A-21 was obtained in a yield of 70% in the same manner asused to synthesize Intermediate A-3, except that Intermediate A-18 wasused instead of Intermediate A-2 and 5′-fluoro-N-phenyl-[1,1′:3′,1″-terphenyl]-4′-amine was used instead of diphenylamine.

Synthesis of Intermediate A-22

Intermediate A-22 was obtained in a yield of 71% in the same manner asused to synthesize Intermediate A-4, except that Intermediate A-21 wasused instead of Intermediate A-3.

Synthesis of Compound 46

Compound 46 was obtained in a yield of 72% in the same manner as used tosynthesize Compound 1, except that Intermediate A-22 was used instead ofIntermediate A-4.

Synthesis Example 8 Synthesis of Compound 53

Synthesis of Intermediate A-1

6,12-dibromochrysene (38.6 g, 100 mmol) was dissolved in 1.5 L ofo-xylene and then the result was heated. When 6,12-dibromochrysene wascompletely dissolved, PdPPh₄ (2.3 g, 5 mmol), K₃PO₄ (42.4 g, 200 mmol),and (4-chloro-2-methoxyphenyl)boronic acid (22.4 g, 120 mmol) were addedthereto, and the resultant mixture was reflux-stirred for 1 hour at atemperature of 140° C. When the temperature was dropped to ambienttemperature, an extraction process was performed thereon using methylenechloride (MC). Column chromatography was performed thereon to obtainIntermediate A-1 (24.6 g, 55 mmol, yield of 55%).

Synthesis of Intermediate A-23

Intermediate A-23 was obtained in a yield of 78% in the same manner asused to synthesize Intermediate A-2, except thatfluoro(naphthalen-1-yl)(phenyl)borane was used instead offluorodiphenylborane.

Synthesis of Intermediate A-24

Intermediate A-24 was obtained in a yield of 76% in the same manner asused to synthesize Intermediate A-3, except that Intermediate A-23 wasused instead of Intermediate A-2 andN-(4-(trimethylsilyl)phenyl)naphthalen-2-amine was used instead ofdiphenylamine.

Synthesis of Intermediate A-25

Intermediate A-25 was obtained in a yield of 79% in the same manner asused to synthesize Intermediate A-4, except that Intermediate A-24 wasused instead of Intermediate A-3.

Synthesis of Compound 53

Compound 53 was obtained in a yield of 82% in the same manner as used tosynthesize Compound 1, except that Intermediate A-25 was used instead ofIntermediate A-4.

Synthesis Example 9 Synthesis of Compound 64

Synthesis of Intermediate A-1

6,12-dibromochrysene (38.6 g, 100 mmol) was dissolved in 1.5 L ofo-xylene and then the result was heated. When 6,12-dibromochrysene wascompletely dissolved, PdPPh₄ (2.3 g, 5 mmol), K₃PO₄ (42.4 g, 200 mmol),and (4-chloro-2-methoxyphenyl)boronic acid (22.4 g, 120 mmol) were addedthereto, and the resultant mixture was reflux-stirred for 1 hour at atemperature of 140° C. When the temperature was dropped to ambienttemperature, an extraction process was performed thereon using methylenechloride (MC). Column chromatography was performed thereon to obtainIntermediate A-1 (24.6 g, 55 mmol, yield of 55%).

Synthesis of Intermediate A-26

Intermediate A-26 was obtained in a yield of 81% in the same manner asused to synthesize Intermediate A-2, except that(3,5-dimethylphenyl)fluoro(naphthalen-1-yl)borane was used instead offluorodiphenylborane.

Synthesis of Intermediate A-27

Intermediate A-27 was obtained in a yield of 76% in the same manner asused to synthesize Intermediate A-3, except that Intermediate A-26 wasused instead of Intermediate A-2 andN-(4-(trimethylsilyl)phenyl)naphthalen-2-amine was used instead ofdiphenylamine.

Synthesis of Intermediate A-28

Intermediate A-28 was obtained in a yield of 80% in the same manner asused to synthesize Intermediate A-4, except that Intermediate A-27 wasused instead of Intermediate A-3.

Synthesis of Compound 64

Compound 64 was obtained in a yield of 85% in the same manner as used tosynthesize Compound 1, except that Intermediate A-28 was used instead ofIntermediate A-4.

Synthesis Example 10 Synthesis of Compound 90

Synthesis of Intermediate A-1

6,12-dibromochrysene (38.6 g, 100 mmol) was dissolved in 1.5 L ofo-xylene and then the result was heated. When 6,12-dibromochrysene wascompletely dissolved, PdPPh₄ (2.3 g, 5 mmol), K₃PO₄ (42.4 g, 200 mmol),and (4-chloro-2-methoxyphenyl)boronic acid (22.4 g, 120 mmol) were addedthereto, and the resultant mixture was reflux-stirred for 1 hour at atemperature of 140° C. When the temperature was dropped to ambienttemperature, an extraction process was performed thereon using methylenechloride (MC). Column chromatography was performed thereon to obtainIntermediate A-1 (24.6 g, 55 mmol, yield of 55%).

Synthesis of Intermediate B-1

Intermediate A-1 (4.5 g, 10 mmol) was dissolved in 100 mL of THF:H₂O(9:1 mixture) and then the mixture was heated. When Intermediate A-1 wascompletely dissolved, PdPPh₄ (222.9 mg, 0.5 mmol), K₂CO₃ (5.5 g, 40mmol), dimesityl(4-(4,4,5,5-tetramethyl-1,3-dioxolan-2-yl)phenyl)borane(6.8 g, 15 mol) were added thereto, and then reflux-stirred for 1 hourat a temperature of 100° C. The temperature was dropped to ambienttemperature, and then an extraction process was performed thereon usingMC. Column chromatography was performed thereon to obtain IntermediateB-1 (4.5 g, 6.5 mmol, yield of 65%).

Synthesis of Intermediate B-2

Intermediate B-2 was obtained in a yield of 84% in the same manner asused to synthesize Intermediate A-3, except that Intermediate B-1 wasused instead of Intermediate A-2.

Synthesis of Intermediate B-3

Intermediate B-3 was obtained in a yield of 88% in the same manner asused to synthesize Intermediate A-4, except that Intermediate B-2 wasused instead of Intermediate A-3.

Synthesis of Compound 90

Compound 90 was obtained in a yield of 88% in the same manner as used tosynthesize Compound 1, except that Intermediate B-3 was used instead ofIntermediate A-4.

Synthesis Example 11 Synthesis of Compound 98

Synthesis of Intermediate A-1

6,12-dibromochrysene (38.6 g, 100 mmol) was dissolved in 1.5 L ofo-xylene and then the result was heated. When 6,12-dibromochrysene wascompletely dissolved, PdPPh₄ (2.3 g, 5 mmol), K₃PO₄ (42.4 g, 200 mmol),and (4-chloro-2-methoxyphenyl)boronic acid (22.4 g, 120 mmol) were addedthereto, and the resultant mixture was reflux-stirred for 1 hour at atemperature of 140° C. When the temperature was dropped to ambienttemperature, an extraction process was performed thereon using methylenechloride (MC). Column chromatography was performed thereon to obtainIntermediate A-1 (24.6 g, 55 mmol, yield of 55%).

Synthesis of Intermediate C-1

Intermediate C-1 was obtained in a yield of 83% in the same manner asused to synthesize Intermediate A-2, except thatdibenzo[b,d]furan-4-ylfluoro(phenyl)borane was used instead offluorodiphenylborane.

Synthesis of Intermediate C-2

Intermediate C-2 was obtained in a yield of 70% in the same manner asused to synthesize Intermediate A-3, except that Intermediate C-1 wasused instead of Intermediate A-2 and (4-(diphenylamino)phenyl)boronicacid was used instead of diphenylamine.

Synthesis of Intermediate C-3

Intermediate C-3 was obtained in a yield of 81% in the same manner asused to synthesize Intermediate A-4, except that Intermediate C-2 wasused instead of Intermediate A-3.

Synthesis of Compound 98

Compound 98 was obtained in a yield of 88% in the same manner as used tosynthesize Compound 1, except that Intermediate C-3 was used instead ofIntermediate A-4.

Synthesis Example 12 Compound 102

Synthesis of Intermediate A-1

6,12-dibromochrysene (38.6 g, 100 mmol) was dissolved in 1.5 L ofo-xylene and then the result was heated. When 6,12-dibromochrysene wascompletely dissolved, PdPPh₄ (2.3 g, 5 mmol), K₃PO₄ (42.4 g, 200 mmol),and (4-chloro-2-methoxyphenyl)boronic acid (22.4 g, 120 mmol) were addedthereto, and the resultant mixture was reflux-stirred for 1 hour at atemperature of 140° C. When the temperature was dropped to ambienttemperature, an extraction process was performed thereon using methylenechloride (MC). Column chromatography was performed thereon to obtainIntermediate A-1 (24.6 g, 55 mmol, yield of 55%).

Synthesis of Intermediate D-1

Intermediate D-1 was obtained in a yield of 66% in the same manner asused to synthesize Intermediate B-1, except thatdimesityl(4-(4,4,5,5-tetramethyl-1,3-dioxolan-2-yl)phenyl)borane wasused instead of fluorodiphenylborane.

Synthesis of Intermediate D-2

Intermediate D-2 was obtained in a yield of 74% in the same manner asused to synthesize Intermediate A-3, except that Intermediate D-1 wasused instead of Intermediate A-2 and (4-(diphenylamino)phenyl)boronicacid was used instead of diphenylamine.

Synthesis of Intermediate D-3

Intermediate D-3 was obtained in a yield of 85% in the same manner asused to synthesize Intermediate A-4, except that Intermediate D-2 wasused instead of Intermediate A-3.

Synthesis of Compound 102

Compound 102 was obtained in a yield of 82% in the same manner as usedto synthesize Compound 1, except that Intermediate D-3 was used insteadof Intermediate A-4.

The compounds synthesized according to Synthesis Examples 1-12 wereconfirmed by ¹H NMR and MS/FAB. Results thereof are shown in Table 1below.

TABLE 1 MS/FAB Compound ¹H NMR (CDCl₃, 400 MHz) calc. found 1 δ =9.28(s, 1H), 8.94(s, 1H), 8.56(d, 1H), 8.4(d, 1H), 649.60 649.26 7.88(d,1H), 7.68(dd, 1H), 7.59(d, 1H), 7.51-7.31(m, 8H), 7.30-7.02(m, 9H),6.82-6.53(m, 4H), 6.43- 6.42(m, 4H) 4 δ = 9.15(s, 1H), 8.84(s, 1H),8.5(d, 1H), 8.26(d, 1H), 755.77 755.34 7.96-7.87(m, 2H), 7.74-7.69(m,2H), 7.65-7.56(m, 3H), 7.54-7.47(m, 4H), 7.38-7.16(m, 3H), 7.03(d, 1H),6.99-6.9(m, 7H), 6.84-6.7(m, 2H), 6.54(d, 1H), 6.53(d, 1H), 2.81(s, 6H),2.72(s, 6H) 14 δ = 9.15(d, 1H), 9.13(d, 1H), 8.48(d, 1H), 8.33(d, 1H),1033.45 1033.12 7.98(d, 1H), 7.8(dd, 1H), 7.71-7.56(m, 8H), 7.54-7.45(m, 8H), 7.43-7.36(m, 5H), 7.34(d, 1H), 7.25- 7.14(m, 7H),7.1-7.03(m, 3H), 6.89(dd, 1H), 6.75(dd, 1H), 6.66-6.59(m, 2H),6.57-6.53(m, 1H), 6.35(d, 1H), 2.35(s, 6H), 2.31(s, 6H) 22 δ = 9.16(s,1H), 8.84(s, 1H), 8.49(d, 1H), 8.33(d, 1H), 753.75 753.32 7.98(d, 1H),7.74(d, 1H), 7.68(dd, 1H), 7.64-7.53(m, 4H), 7.5-7.46(m, 3H),7.44-7.4(m, 3H), 7.33-7.3(m, 5H), 7.24-7.22(m, 2H), 7.13-7.1(m, 3H),6.95-6.91(m, 2H), 6.74(d, 1H), 6.59(d, 1H), 6.46(dd, 1H), 6.27(dd, 1H),6.18(dd, 1H), 2.7(s, H) 25 δ = 9.16(s, 1H), 8.85(s, 1H), 8.49(d, 1H),8.36(d, 1H), 699.66 699.27 7.94(d, H), 7.88-7.85(m, 2H), 7.86(d, 1H),7.86(d, 1H), 7.68(d, 1H), 7.62-7.58(m, 2H), 7.57-7.4(m, 8H),7.34-7.31(m, 3H), 7.15-7.13(m, 4H), 6.86(d, 1H), 6.77(d, 1H), 6.77(d,1H), 6.64(d, 1H), 6.45-6.41(m, 4H) 33 δ = 9.24(s, 1H), 8.83(s, 1H),8.54(d, 1H), 8.28(d, 1H), 926.02 925.45 8.1(d, 1H), 7.76(d, 1H),7.69-7.66(m, 1H), 7.63- 7.52(m, 7H), 7.5-7.45(m, 2H), 7.43-7.4(m, 1H),7.31- 7.25(m, 2H), 7.19-7.07(m, 3H), 7.05-6.78(m, 7H), 6.6(dd, 1H),6.54(dd, 1H), 6.37(dd, 1H), 2.49(s, 3H), 2.49(s, 3H), 2.44(s, 3H),2.44(s, 3H), 2.39(s, 3H), 2.39(s, 3H), 1.99(s, 6H) 46 δ = 8.84(s, 1H),8.54(d, 1H), 8.29(d, 1H), 8.1(d, 1H), 903.95 903.40 7.72-7.62(m, 6H),7.55-7.53(m, 5H), 7.48-7.43(m, 3H), 7.38-7.29(m, 2H), 7.17-7.08(m, 3H),6.89- 6.84(m, 4H), 6.7-6.29(m, 5H), 2.49(s, 3H), 2.49(s, 3H), 2.49(s,3H), 2.49(s, 3H), 2.47(s, 3H), 2.47(s, 3H) 53 δ = 9.22(s, 1H), 8.89(s,1H), 8.52(d, 1H), 8.35(d, 1H), 821.90 821.33 8.2(d, 1H), 7.99-7.74(m,5H), 7.67-7.5(m, 5H), 7.48- 7.42(m, 5H), 7.41-7.36(m, 5H), 7.31-7.26(m,5H), 6.9- 6.84(m, 2H), 6.79-6.76(m, 2H), 6.62(dd, 1H), 0.24(s, 9H) 64 δ= 9.23(s, 1H), 8.9(s, 1H), 8.53(d, 1H), 8.38(d, 1H), 893.89 893.358.23(d, 1H), 7.99-7.91(m, 2H), 7.82-7.75(m, 3H), 7.71-7.55(m, 8H),7.5-7.36(m, 8H), 7.29-7.14(m, 3H), 7.14-6.85(m, 5H), 6.74-6.71(m, 2H),6.52-6.38(m, 2H), 2.4(s, 6H) 90 δ = 9.24(s, 1H), 9.01(s, 1H), 8.83(d,1H), 8.43(d, 1H), 809.86 809.38 7.83(d, 1H), 7.78-7.56(m, 6H),7.43-7.29(m, 3H), 7.11-6.81(m, 9H), 6.72-6.58(m, 3H), 6.39-6.29(m, 4H),2.19(s, 3H), 2.19(s, 3H), 2.19(s, 3H), 2.19(s, 3H), 2.18(s, 3H), 2.18(s,3H) 98 δ = 9.42(s, 1H), 9.06(s, 1H), 8.56(d, 1H), 8.31(d, 1H), 891.88891.33 8-7.83(m, 4H), 7.69-7.53(m, 7H), 7.49-7.42(m, 6H), 7.41-7.33(m,6H), 7.29-7.24(m, 3H), 7.21-7.14(m, 3H), 7.06-6.85(m, 4H), 6.66(dd, 1H),6.39-6.33(m, 2H), 6.1-6.04(m, 2H), 6.04(, H) 102 δ = 9.8(s, 1H), 9.04(s,1H), 8.85(d, 1H), 8.44(d, 1H), 885.96 885.41 7.98(d, 1H), 7.82-7.51(m,7H), 7.44-7.36(m, 5H), 7.17-7.07(m, 5H), 6.88-6.65(m, 8H), 6.19-6.14(m,4H), 2.19(s, 3H), 2.19(s, 3H), 2.19(s, 3H), 2.19(s, 3H), 2.18(s, 3H),2.18(s, 3H)

Example 1

A 15 Ωcm² (1,200 Å) ITO glass substrate (a product of Corning) was cutto a size of 50 mm×50 mm×0.7 mm, and was ultrasonically cleaned by usingisopropyl alcohol and pure water for 5 minutes each, and then UV lightwas irradiated thereto for 30 minutes and exposed to ozone to clean.Then, the resultant structure was loaded into a vacuum depositionapparatus.

4,4′-Bis[N-phenyl-N-(9-phenylcarbazol-3-yl)amino]-1,1′-biphenyl (HT13)was vacuum deposited on the ITO glass substrate to form a hole injectionlayer having a thickness of 600 Å, andN-[1,1′-biphenyl]-4-yl-9,9-dimethyl-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]-9H-fluorene-2-amine(HT3) was vacuum deposited on the hole injection layer to form a holetransport layer having a thickness of 300 Å, thereby completing theformation of a hole transport region.

9,10-di-naphthalene-2-yl-anthracene (ADN), as a host, Compound 1, as adopant, were co-deposited on the hole transport region at a weight ratioof 98:2 to form an emission layer having a thickness of 300 Å.

Alq₃ was vacuum-deposited on the emission layer to form an electrontransport layer having a thickness of 300 Å, and LiF was deposited onthe electron transport layer to form an electron injection layer havinga thickness of 10 Å, thereby completing the formation of an electrontransport region.

Al was vacuum-deposited on the electron transport region to form acathode having a thickness of 3,000 Å, thereby completing themanufacture of an organic light-emitting device.

Example 2

An organic light-emitting device was manufactured in the same manner asin Example 1, except that in forming the emission layer, as a dopant,Compound 4 was used instead of Compound 1.

Example 3

An organic light-emitting device was manufactured in the same manner asin Example 1, except that in forming the emission layer, as a dopant,Compound 14 was used instead of Compound 1.

Example 4

An organic light-emitting device was manufactured in the same manner asin Example 1, except that in forming the emission layer, as a dopant,Compound 22 was used instead of Compound 1.

Example 5

An organic light-emitting device was manufactured in the same manner asin Example 1, except that in forming the emission layer, as a dopant,Compound 25 was used instead of Compound 1.

Example 6

An organic light-emitting device was manufactured in the same manner asin Example 1, except that in forming the emission layer, as a dopant,Compound 33 was used instead of Compound 1.

Example 7

An organic light-emitting device was manufactured in the same manner asin Example 1, except that in forming an emission layer, as a dopant,Compound 46 was used instead of Compound 1.

Example 8

An organic light-emitting device was manufactured in the same manner asin Example 1, except that in forming the emission layer, as a dopant,Compound 53 was used instead of Compound 1.

Example 9

An organic light-emitting device was manufactured in the same manner asin Example 1, except that in forming the emission layer, as a dopant,Compound 64 was used instead of Compound 1.

Example 10

An organic light-emitting device was manufactured in the same manner asin Example 1, except that in forming the emission layer, as a dopant,Compound 90 was used instead of Compound 1.

Example 11

An organic light-emitting device was manufactured in the same manner asin Example 1, except that in forming the emission layer, as a dopant,Compound 98 was used instead of Compound 1.

Example 12

An organic light-emitting device was manufactured in the same manner asin Example 1, except that in forming an emission layer, as a dopant,Compound 102 was used instead of Compound 1.

Comparative Example 1

An organic light-emitting device was manufactured in the same manner asin Example 1, except that in forming the emission layer, as a dopant,Compound A was used instead of Compound 1.

Comparative Example 2

An organic light-emitting device was manufactured in the same manner asin Example 1, except that in forming the emission layer, as a dopant,Compound B was used instead of Compound 1.

Evaluation Example 1

The driving voltage, current density, brightness, efficiency, andhalf-lifespan of the organic light-emitting devices manufacturedaccording to Examples 1 to 12, and Comparative Examples 1 and 2 weremeasured by using Kethley SMU 236 and a brightness photometer PR650, andresults thereof are shown in Table 2. The half-lifespan is a period oftime that lapses until the brightness of the organic light-emittingdevice was 50% of initial brightness.

TABLE 2 Driving Current Half lifespan voltage density BrightnessEfficiency Emission (hr@100 Emission layer (V) (mA/cm²) (cd/m²) (cd/A)color mA/cm²) Example 1 Compound 1 6.82 50 3,311 6.43 Blue 378 Example 2Compound 4 6.67 50 3,429 6.65 Blue 351 Example 3 Compound 14 5.71 503,263 6.37 Blue 299 Example 4 Compound 22 5.88 50 3,443 6.66 Blue 354Example 5 Compound 25 5.68 50 3,312 6.42 Blue 332 Example 6 Compound 336.65 50 3,388 6.57 Blue 362 Example 7 Compound 46 6.63 50 3,491 6.75Blue 385 Example 8 Compound 53 6.60 50 3,483 6.73 Blue 390 Example 9Compound 64 5.99 50 3,432 6.69 Blue 352 Example 10 Compound 90 5.85 503,369 6.51 Blue 365 Example 11 Compound 98 6.73 50 3,150 6.30 Blue 331Example 12 Compound 102 6.76 50 3,170 6.34 Blue 309 Comparative CompoundA 7.01 50 2,645 5.29 Blue 258 Example 1 Comparative Compound B 6.99 502,950 5.3 Blue 295 Example 2

From Table 2, it may be seen that the organic light-emitting devicesmanufactured according to Examples 1 to 11 had higher driving voltage,higher brightness, higher efficiency, and longer half-lifespan than theorganic light-emitting devices manufactured according to ComparativeExamples 1 and 2.

An organic light-emitting device including the compound according to anembodiment may have a low driving voltage, high efficiency, highbrightness, and long lifespan.

Example embodiments have been disclosed herein, and although specificterms are employed, they are used and are to be interpreted in a genericand descriptive sense only and not for purpose of limitation. In someinstances, as would be apparent to one of ordinary skill in the art asof the filing of the present application, features, characteristics,and/or elements described in connection with a particular embodiment maybe used singly or in combination with features, characteristics, and/orelements described in connection with other embodiments unless otherwisespecifically indicated. Accordingly, it will be understood by those ofskill in the art that various changes in form and details may be madewithout departing from the spirit and scope of the present invention asset forth in the following claims.

What is claimed is:
 1. A condensed cyclic compound represented byFormula 1 below:

wherein, in Formula 1, X₁ is O or S; R₁ to R₁₄ are each independentlyselected from a group represented by the following Formula 2, a grouprepresented by the following Formula 3, a hydrogen, a deuterium, —F,—Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an aminogroup, an amidino group, a hydrazine group, a hydrazone group, acarboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, aphosphoric acid or a salt thereof, a substituted or unsubstituted C₁-C₆₀alkyl group, a substituted or unsubstituted C₂-C₆₀ alkenyl group, asubstituted or unsubstituted C₂-C₆₀ alkynyl group, a substituted orunsubstituted C₁-C₆₀ alkoxy group, a substituted or unsubstituted C₃-C₁₀cycloalkyl group, a substituted or unsubstituted C₁-C₁₀ heterocycloalkylgroup, a substituted or unsubstituted C₃-C₁₀ cycloalkenyl group, asubstituted or unsubstituted C₁-C₁₀ heterocycloalkenyl group, asubstituted or unsubstituted C₆-C₆₀ aryl group, a substituted orunsubstituted C₆-C₆₀ aryloxy group, a substituted or unsubstitutedC₆-C₆₀ arylthio group, a substituted or unsubstituted C₁-C₆₀ heteroarylgroup, a substituted or unsubstituted monovalent non-aromatic condensedpolycyclic group, a substituted or unsubstituted monovalent non-aromaticcondensed heteropolycyclic group, and —Si(Q₁)(Q₂)(Q₃); at least one ofR₁ to R₁₄ is a group represented by Formula 2, and at least one of R₁ toR₁₄ is a group represented by Formula 3:

wherein in Formulae 2 and 3, L₁ and L₂ are each independently selectedfrom a substituted or unsubstituted C₃-C₁₀ cycloalkylene, a substitutedor unsubstituted C₁-C₁₀ heterocycloalkylene, a substituted orunsubstituted C₃-C₁₀ cycloalkenylene, a substituted or unsubstitutedC₁-C₁₀ heterocycloalkenylene, a substituted or unsubstituted C₆-C₆₀arylene, a substituted or unsubstituted C₁-C₆₀ heteroarylene, asubstituted or unsubstituted divalent non-aromatic condensed polycyclicgroup, and a substituted or unsubstituted divalent non-aromaticcondensed heteropolycyclic group; a1 and a2 are each independentlyselected from 0, 1, 2 and 3, when a1 is 2 or more, two or more L₁ areidentical or different from one another, and when a2 is 2 or more, twoor more L₂ are identical or different from one another; Ar₁ to Ar₄ areeach independently selected from a substituted or unsubstituted C₃-C₁₀cycloalkyl group, a substituted or unsubstituted C₁-C₁₀ heterocycloalkylgroup, a substituted or unsubstituted C₃-C₁₀ cycloalkenyl group, asubstituted or unsubstituted C₁-C₁₀ heterocycloalkenyl group, asubstituted or unsubstituted C₆-C₆₀ aryl group, a substituted orunsubstituted C₁-C₆₀ heteroaryl group, a substituted or unsubstitutedmonovalent non-aromatic condensed polycyclic group, and a substituted orunsubstituted monovalent non-aromatic condensed heteropolycyclic group;wherein at least one substituent of the substituted C₃-C₁₀ cycloalkylenegroup, substituted C₁-C₁₀ heterocycloalkylene group, substituted C₃-C₁₀cycloalkenylene group, substituted C₁-C₁₀ heterocycloalkenylene group,substituted C₆-C₆₀ arylene group, substituted C₁-C₆₀ heteroarylenegroup, substituted divalent non-aromatic condensed polycyclic group,substituted divalent non-aromatic condensed heteropolycyclic group,substituted C₁-C₆₀ alkyl group, substituted C₂-C₆₀ alkenyl group,substituted C₂-C₆₀ alkynyl group, substituted C₁-C₆₀ alkoxy group,substituted C₃-C₁₀ cycloalkyl group, substituted C₁-C₁₀ heterocycloalkylgroup, substituted C₃-C₁₀ cycloalkenyl group, substituted C₁-C₁₀heterocycloalkenyl group, substituted C₆-C₆₀ aryl group, substitutedC₆-C₆₀ aryloxy group, substituted C₆-C₆₀ arylthio group, substitutedC₁-C₆₀ heteroaryl group, substituted monovalent non-aromatic condensedpolycyclic group, and substituted monovalent non-aromatic condensedheteropolycyclic group is selected from: a deuterium, —F, —Cl, —Br, —I,a hydroxyl group, a cyano group, a nitro group, an amino group, anamidino group, a hydrazine group, a hydrazone group, a carboxylic acidor a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acidor a salt thereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, aC₂-C₆₀ alkynyl group, and a C₁-C₆₀ alkoxy group; a C₁-C₆₀ alkyl group, aC₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, and a C₁-C₆₀ alkoxy group,each substituted with at least one selected from a deuterium, —F, —Cl,—Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group,an amidino group, a hydrazine group, a hydrazone group, a carboxylicacid group or a salt thereof, a sulfonic acid group or a salt thereof, aphosphoric acid group or a salt thereof, a C₃-C₁₀ cycloalkyl group, aC₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, aC₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, a monovalentnon-aromatic condensed polycyclic group, a monovalent non-aromaticcondensed heteropolycyclic group, and —Si(Q₁₁)(Q₁₂)(Q₁₃); aC₃-C₁₀cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,and a monovalent non-aromatic heterocondensed polycyclic group; a C₃-C₁₀cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenylgroup, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, amonovalent non-aromatic condensed polycyclic group, and a monovalentnon-aromatic heterocondensed polycyclic group, each substituted with atleast one selected from a deuterium, —F, —Cl, —Br, —I, a hydroxyl group,a cyano group, a nitro group, an amino group, an amidino group, ahydrazine group, a hydrazone group, a carboxylic acid group or a saltthereof, a sulfonic acid group or a salt thereof, a phosphoric acidgroup or a salt thereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, aC₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀cycloalkyl group, aC₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, aC₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, a monovalentnon-aromatic condensed polycyclic group, a monovalent non-aromaticheterocondensed polycyclic group, and —Si(Q₂₁)(Q₂₂)(Q₂₃); and—Si(Q₃₁)(Q₃₂)(Q₃₃),    wherein Q₁ to Q₃, Q₁₁ to Q₁₃, Q₂₁ to Q₂₃, and Q₃₁to Q₃₃ are each independently selected from a hydrogen, a deuterium, —F,—Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an aminogroup, an amidino group, a hydrazine group, a hydrazone group, acarboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, aphosphoric acid or a salt thereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, aC₃-C₁₀cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, aC₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀aryl group, a C₁-C₆₀ heteroaryl group, a monovalent non-aromaticcondensed polycyclic group, and a monovalent non-aromatic condensedheteropolycyclic group.
 2. The condensed cyclic compound as claimed inclaim 1, wherein L₁ and L₂ are each independently selected from: aphenylene group, a pentalenylene group, an indenylene group, anaphthylene group, an azulenylene group, a heptalenylene group, anindacenylene group, an acenaphthylene group, a fluorenylene group, aspiro-fluorenylene group, a benzofluorenylene group, adibenzofluorenylene group, a phenalenylene group, a phenanthrenylenegroup, an anthracenylene group, a fluoranthenylene group, atriphenylenylene group, a pyrenylene group, a chrysenylene group, anaphthacenylene group, a picenylene group, a perylenylene group, apentaphenylene group, a hexacenylene group, a pentacenylene group, arubicenylene group, a coronenylene group, an ovalenylene group, apyrrolylene group, a thiophenylene group, a furanylene group, animidazolylene group, a pyrazolylene group, a thiazolylene group, anisothiazolylene group, an oxazolylene group, a isoxazolylene group, apyridinylene group, a pyrazinylene group, a pyrimidinylene group, apyridazinylene group, an isoindolylene group, an indolylene group, anindazolylene group, a purinylene group, a quinolinylene group, anisoquinolinylene group, a benzoquinolinylene group, a phthalazinylenegroup, a naphthyridinylene group, a quinoxalinylene group, aquinazolinylene group, a cinnolinylene group, a carbazolylene group, aphenanthridinylene group, an acridinylene group, a phenanthrolinylenegroup, a phenazinylene group, a benzoimidazolylene group, abenzofuranylene group, a benzothiophenylene group, anisobenzothiazolylene group, a benzoxazolylene group, anisobenzoxazolylene group, a triazolylene group, a tetrazolylene group,an oxadiazolylene group, a triazinylene group, a dibenzofuranylenegroup, a dibenzothiophenylene group, a benzocarbazolylene group, adibenzocarbazolylene group, a thiadiazolylene group, animidazopyridinylene group, and an imidazopyrimidinylene group; and aphenylene group, a pentalenylene group, an indenylene group, anaphthylene group, an azulenylene group, a heptalenylene group, anindacenylene group, an acenaphthylene group, a fluorenylene group, aspiro-fluorenylene group, a benzofluorenylene group, adibenzofluorenylene group, a phenalenylene group, a phenanthrenylenegroup, an anthracenylene group, a fluoranthenylene group, atriphenylenylene group, a pyrenylene group, a chrysenylene group, anaphthacenylene group, a picenylene group, a perylenylene group, apentaphenylene group, a hexacenylene group, a pentacenylene group, arubicenylene group, a coronenylene group, ovalenylene group, apyrrolylene group, a thiophenylene group, a furanylene group, animidazolylene group, a pyrazolylene group, a thiazolylene group, anisothiazolylene group, an oxazolylene group, a isoxazolylene group, apyridinylene group, a pyrazinylene group, a pyrimidinylene group, apyridazinylene group, an isoindolylene group, an indolylene group, anindazolylene group, a purinylene group, a quinolinylene group, anisoquinolinylene group, a benzoquinolinylene group, a phthalazinylenegroup, a naphthyridinylene group, a quinoxalinylene group, aquinazolinylene group, a cinnolinylene group, a carbazolylene group, aphenanthridinylene group, an acridinylene group, a phenanthrolinylenegroup, a phenazinylene group, a benzoimidazolylene group, abenzofuranylene group, a benzothiophenylene group, anisobenzothiazolylene group, a benzoxazolylene group, anisobenzoxazolylene group, a triazolylene group, a tetrazolylene group,an oxadiazolylene group, a triazinylene group, a dibenzofuranylenegroup, a dibenzothiophenylene group, a benzocarbazolylene group, adibenzocarbazolylene group, a thiadiazolylene group, animidazopyridinylene group, and an imidazopyrimidinylene group, eachsubstituted with at least one selected from a deuterium, —F, —Cl, —Br,—I, a hydroxyl group, a cyano group, a nitro group, an amino group, anamidino group, a hydrazine group, a hydrazone group, a carboxylic acidor a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acidor a salt thereof, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, acyclopentyl group, a cyclohexyl group, a cycloheptyl group, acyclopentenyl group, a cyclohexenyl group, a phenyl group, a pentalenylgroup, an indenyl group, a naphthyl group, an azulenyl group, aheptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenylgroup, a spiro-fluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, ananthracenyl group, a fluoranthenyl group, a triphenylenyl group, apyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group,a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenylgroup, a rubicenyl group, a coronenyl group, an ovalenyl group, apyrrolyl group, a thiophenyl group, a furanyl group, an imidazolylgroup, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, anoxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinylgroup, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, anindolyl group, an indazolyl group, a purinyl group, a quinolinyl group,an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, anaphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, acinnolinyl group, a carbazolyl group, a phenanthridinyl group, anacridinyl group, a phenanthrolinyl group, a phenazinyl group, abenzoimidazolyl group, a benzofuranyl group, a benzothiophenyl group, anisobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group,a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinylgroup, a dibenzofuranyl group, a dibenzothiophenyl group, abenzocarbazolyl group, a dibenzocarbazolyl group, a thiadiazolyl group,an imidazopyridinyl group, and an imidazopyrimidinyl group.
 3. Thecondensed cyclic compound as claimed in claim 1, wherein L₁ and L₂ areeach independently a group represented by one of the following Formulae3-1 to 3-35:

wherein, in Formulae 3-1 to 3-35, Y₁ is O, S, C(Z₃)(Z₄), N(Z₅), orSi(Z₆)(Z₇); Z₁ to Z₇ are each independently selected from a hydrogen, adeuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine group, a hydrazonegroup, a carboxylic acid or a salt thereof, a sulfonic acid or a saltthereof, a phosphoric acid or a salt thereof, a C₁ to C₂₀ alkyl group, aC₁ to C₂₀ alkoxy group, a phenyl group, a naphthyl group, a fluorenylgroup, a spiro-fluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, apyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group,a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, anisoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, acarbazolyl group, and a triazinyl group, d1 is an integer selected from1, 2, 3, and 4, d2 is an integer selected from 1, 2, and 3, d3 is aninteger selected from 1, 2, 3, 4, 5, and 6, d4 is an integer selectedfrom 1, 2, 3, 4, 5, 6, 7, and 8, d5 is 1 or 2, and d6 is an integerselected from 1, 2, 3, 4, and 5, and * and *′ indicate binding sites toa neighboring atom.
 4. The condensed cyclic compound as claimed in claim1, wherein L₁ and L₂ are each independently a group represented by oneof the following Formulae 4-1 to 4-29:

wherein, in Formulae 4-1 to 4-29, * and *′ indicate a binding site to aneighboring atom.
 5. The condensed cyclic compound as claimed in claim1, wherein a1 and a2 are each independently 0 or
 1. 6. The condensedcyclic compound as claimed in claim 1, wherein Ar₁ to Ar₄ are eachindependently selected from: a phenyl group, a pentalenyl group, anindenyl group, a naphthyl group, an azulenyl group, a heptalenyl group,an indacenyl group, an acenaphthyl group, a fluorenyl group, aspiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group,a phenalenyl group, a phenanthrenyl group, an anthracenyl group, afluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenylgroup, a naphthacenyl group, a picenyl group, a perylenyl group, apentaphenyl group, a hexacenyl group, a pentacenyl group, a rubicenylgroup, a coronenyl group, an ovalenyl group, a pyrrolyl group, athiophenyl group, a furanyl group, an imidazolyl group, a pyrazolylgroup, a thiazolyl group, an isothiazolyl group, an oxazolyl group, anisoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinylgroup, a pyridazinyl group, an isoindolyl group, an indolyl group, anindazolyl group, a purinyl group, a quinolinyl group, an isoquinolinylgroup, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinylgroup, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, acarbazolyl group, a phenanthridinyl group, an acridinyl group, aphenanthrolinyl group, a phenazinyl group, a benzoimidazolyl group, abenzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group,a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, atetrazolyl group, an oxadiazolyl group, a triazinyl group, adibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolylgroup, a dibenzocarbazolyl group, a dibenzosilolyl group, a thiadiazolylgroup, an imidazopyridinyl group, and an imidazopyrimidinyl group; aphenyl group, a pentalenyl group, an indenyl group, a naphthyl group, anazulenyl group, a heptalenyl group, an indacenyl group, an acenaphthylgroup, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenylgroup, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenylgroup, an anthracenyl group, a fluoranthenyl group, a triphenylenylgroup, a pyrenyl group, a chrysenyl group, a naphthacenyl group, apicenyl group, a perylenyl group, a pentaphenyl group, a hexacenylgroup, a pentacenyl group, a rubicenyl group, a coronenyl group, anovalenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group,an imidazolyl group, a pyrazolyl group, a thiazolyl group, anisothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinylgroup, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, anisoindolyl group, an indolyl group, an indazolyl group, a purinyl group,a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, aphthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, aquinazolinyl group, a cinnolinyl group, a carbazolyl group, aphenanthridinyl group, an acridinyl group, a phenanthrolinyl group, aphenazinyl group, a benzoimidazolyl group, a benzofuranyl group, abenzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group,an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, anoxadiazolyl group, a triazinyl group, a dibenzofuranyl group, adibenzothiophenyl group, a benzocarbazolyl group, a dibenzosilolylgroup, a dibenzocarbazolyl group, a thiadiazolyl group, animidazopyridinyl group, and an imidazopyrimidinyl group, eachsubstituted with at least one selected from a deuterium, —F, —Cl, —Br,—I, a hydroxyl group, a cyano group, a nitro group, an amino group, anamidino group, a hydrazine group, a hydrazone group, a carboxylic acidor a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acidor a salt thereof, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, acyclopentyl group, a cyclohexyl group, a cycloheptyl group, acyclopentenyl group, a cyclohexenyl group, a phenyl group, a pentalenylgroup, an indenyl group, a naphthyl group, an azulenyl group, aheptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenylgroup, a spiro-fluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, ananthracenyl group, a fluoranthenyl group, a triphenylenyl group, apyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group,a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenylgroup, a rubicenyl group, a coronenyl group, an ovalenyl group, apyrrolyl group, a thiophenyl group, a furanyl group, an imidazolylgroup, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, anoxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinylgroup, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, anindolyl group, an indazolyl group, a purinyl group, a quinolinyl group,an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, anaphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, acinnolinyl group, a carbazolyl group, a phenanthridinyl group, anacridinyl group, a phenanthrolinyl group, a phenazinyl group, abenzoimidazolyl group, a benzofuranyl group, a benzothiophenyl group, anisobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group,a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinylgroup, a dibenzofuranyl group, a dibenzothiophenyl group, abenzocarbazolyl group and a dibenzocarbazolyl group, a thiadiazolylgroup, an imidazopyridinyl group, an imidazopyrimidinyl group, and—Si(Q₃₁)(Q₃₂)(Q₃₃); and wherein Q₃₁ to Q₃₃ are each independentlyselected from a C₁-C₁₀ alkyl group, a C₁-C₁₀alkoxy group, a phenylgroup, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, abenzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group,an anthracenyl group, a triphenylenyl group, a pyrenyl group, achrysenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group,an imidazolyl group, a pyrazolyl group, a thiazolyl group, anisothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinylgroup, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, aquinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, aquinoxalinyl group, a quinazolinyl group, a carbazolyl group, aphenanthrolinyl group, a benzoimidazolyl group, a benzofuranyl group, abenzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group,an isobenzoxazolyl group, a triazolyl group, an oxadiazolyl group, atriazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, abenzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolylgroup, a thiadiazolyl group, an imidazopyridinyl group, and animidazopyrimidinyl group.
 7. The condensed cyclic compound as claimed inclaim 1, wherein Ar₁ to Ar₄ are each independently selected from: aphenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenylgroup, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenylgroup, an anthracenyl group, a triphenylenyl group, a pyrenyl group, achrysenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group,an imidazolyl group, a pyrazolyl group, a thiazolyl group, anisothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinylgroup, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, aquinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, aquinoxalinyl group, a quinazolinyl group, a carbazolyl group, abenzoimidazolyl group, a benzofuranyl group, a benzothiophenyl group, anisobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group,an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, adibenzothiophenyl group, an imidazopyridinyl group, and animidazopyrimidinyl group; and a phenyl group, a naphthyl group, afluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, atriphenylenyl group, a pyrenyl group, a chrysenyl group, a pyrrolylgroup, a thiophenyl group, a furanyl group, an imidazolyl group, apyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolylgroup, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, apyrimidinyl group, a pyridazinyl group, a quinolinyl group, anisoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, aquinazolinyl group, a carbazolyl group, a benzoimidazolyl group, abenzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group,a benzoxazolyl group, an isobenzoxazolyl group, an oxadiazolyl group, atriazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, animidazopyridinyl group, and an imidazopyrimidinyl group, eachsubstituted with at least one selected from a deuterium, —F, —Cl, —Br,—I, a hydroxyl group, a cyano group, a nitro group, an amino group, anamidino group, a hydrazine group, a hydrazone group, a carboxylic acidor a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acidor a salt thereof, a C₁-C₁₀ alkyl group, a C₁-C₁₀ alkoxy group, a phenylgroup, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, abenzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group,an anthracenyl group, a triphenylenyl group, a pyrenyl group, achrysenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group,an imidazolyl group, a pyrazolyl group, a thiazolyl group, anisothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinylgroup, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, aquinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, aquinoxalinyl group, a quinazolinyl group, a carbazolyl group, abenzoimidazolyl group, a benzofuranyl group, a benzothiophenyl group, anisobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group,an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, adibenzothiophenyl group, an imidazopyridinyl group, animidazopyrimidinyl group, and —Si(Q₃₁)(Q₃₂)(Q₃₃), wherein Q₃₁ to Q₃₃ areeach independently selected from a C₁-C₁₀ alkyl group, a C₁-C₁₀alkoxygroup, a phenyl group, and a naphthyl group.
 8. The condensed cycliccompound as claimed in claim 1, wherein Ar₁ to Ar₄ are eachindependently selected from: a phenyl group, a naphthyl group, afluorenyl group, a phenanthrenyl group, a pyridinyl group, a pyrimidinylgroup, a triazinyl group, a dibenzofuranyl group, and adibenzothiophenyl group; and a phenyl group, a naphthyl group, afluorenyl group, a phenanthrenyl group, a pyridinyl group, a pyrimidinylgroup, a triazinyl group, a dibenzofuranyl group, and adibenzothiophenyl group, each substituted with at least one selectedfrom a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, anitro group, an amino group, an amidino group, a hydrazine group, ahydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid ora salt thereof, a phosphoric acid or a salt thereof, a C₁-C₁₀ alkylgroup, a C₁-C₁₀ alkoxy group, a phenyl group, a naphthyl group, afluorenyl group, a phenanthrenyl group, a pyridinyl group, a pyrimidinylgroup, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenylgroup, and —Si(Q₃₁)(Q₃₂)(Q₃₃), wherein Q₃₁ to Q₃₃ are each independentlyselected from a C₁-C₁₀ alkyl group, a C₁-C₁₀ alkoxy group, a phenylgroup, and a naphthyl group.
 9. The condensed cyclic compound as claimedin claim 1, wherein R₁ to R₁₄ are each independently selected from: agroup represented by Formula 2, a group represented by Formula 3, ahydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyanogroup, a nitro group, an amino group, an amidino group, a hydrazinegroup, a hydrazone group, a carboxylic acid or a salt thereof, asulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, aC₁-C₂₀ alkyl group, and a C₁-C₂₀ alkoxy group; a phenyl group, anaphthyl group, a fluorenyl group, a spiro-fluorenyl group, abenzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group,an anthracenyl group, a triphenylenyl group, a pyrenyl group, achrysenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group,an imidazolyl group, a pyrazolyl group, a thiazolyl group, anisothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinylgroup, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, aquinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, aquinoxalinyl group, a quinazolinyl group, a carbazolyl group, abenzoimidazolyl group, a benzofuranyl group, a benzothiophenyl group, anisobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group,an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, adibenzothiophenyl group, an imidazopyridinyl group, and animidazopyrimidinyl group; a phenyl group, a naphthyl group, a fluorenylgroup, a spiro-fluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, atriphenylenyl group, a pyrenyl group, a chrysenyl group, a pyrrolylgroup, a thiophenyl group, a furanyl group, an imidazolyl group, apyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolylgroup, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, apyrimidinyl group, a pyridazinyl group, a quinolinyl group, anisoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, aquinazolinyl group, a carbazolyl group, a benzoimidazolyl group, abenzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group,a benzoxazolyl group, an isobenzoxazolyl group, an oxadiazolyl group, atriazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, animidazopyridinyl group, and an imidazopyrimidinyl group, eachsubstituted with at least one selected from a deuterium, —F, —Cl, —Br,—I, a hydroxyl group, a cyano group, a nitro group, an amino group, anamidino group, a hydrazine group, a hydrazone group, a carboxylic acidor a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acidor a salt thereof, a C₁-C₁₀ alkyl group, a C₁-C₁₀ alkoxy group, a phenylgroup, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, abenzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group,an anthracenyl group, a triphenylenyl group, a pyrenyl group, achrysenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group,an imidazolyl group, a pyrazolyl group, a thiazolyl group, anisothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinylgroup, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, aquinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, aquinoxalinyl group, a quinazolinyl group, a carbazolyl group, abenzoimidazolyl group, a benzofuranyl group, a benzothiophenyl group, anisobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group,an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, adibenzothiophenyl group, an imidazopyridinyl group, animidazopyrimidinyl group, and —Si(Q₃₁)(Q₃₂)(Q₃₃); and —Si(Q₁)(Q₂)(Q₃),wherein Q₁ to Q₃ and Q₃₁ to Q₃₃ are each independently selected from aC₁-C₁₀alkyl group, a C₁-C₁₀alkoxy group, a phenyl group, and a naphthylgroup.
 10. The condensed cyclic compound as claimed in claim 1, whereinR₁ to R₁₄ are each independently selected from a group represented byFormula 2, a group represented by Formula 3, a hydrogen, a deuterium,—F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, anamino group, an amidino group, a hydrazine group, a hydrazone group, acarboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, aphosphoric acid or a salt thereof, a C₁-C₁₀ alkyl group, and a C₁-C₁₀alkoxy group; a phenyl group, a naphthyl group, a pyrimidinyl group, anda triazinyl group; a phenyl group, a naphthyl group, a pyridinyl group,a pyrimidinyl group, and a triazinyl group, each substituted with atleast one selected from a deuterium, —F, —Cl, —Br, —I, a hydroxyl group,a cyano group, a nitro group, an amino group, an amidino group, ahydrazine group, a hydrazone group, a carboxylic acid or a salt thereof,a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof,a C₁-C₁₀ alkyl group, a C₁-C₁₀ alkoxy group, a phenyl group, a naphthylgroup, a pyridinyl group, a pyrimidinyl group, a triazinyl group, and—Si(Q₃₁)(Q₃₂)(Q₃₃); and —Si(Q₁)(Q₂)(Q₃), wherein Q₁ to Q₃ and Q₃₁ to Q₃₃are each independently selected from a C₁-C₁₀ alkyl group, a C₁-C₁₀alkoxy group, a phenyl group, and a naphthyl group.
 11. The condensedcyclic compound as claimed in claim 1, wherein Ar₁ to Ar₄ are eachindependently a group represented by one of the following Formulae 5-1to 5-43, and R₁ to R₁₄ are each independently selected from a grouprepresented by Formula 2, a group represented by Formula 3, a hydrogen,a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine group, a hydrazonegroup, a carboxylic acid or a salt thereof, a sulfonic acid or a saltthereof, a phosphoric acid or a salt thereof, a C₁-C₂₀ alkyl group, aC₁-C₂₀ alkoxy group, —Si(Q₁)(Q₂)(Q₃), and a group represented by one ofthe following Formulae 5-1 to 5-43, wherein Q₁ to Q₃ are eachindependently selected from a C₁-C₁₀ alkyl group, a C₁-C₁₀ alkoxy group,a phenyl group, and a naphthyl group:

wherein, in Formulae 5-1 to 5-43, Y₃₁ is O, S, C(Z₃₃)(Z₃₄), N(Z₃₅), orSi(Z₃₆)(Z₃₇); Z₃₁ to Z₃₇ are each independently selected from ahydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyanogroup, a nitro group, an amino group, an amidino group, a hydrazinegroup, a hydrazone group, a carboxylic acid or a salt thereof, asulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, aC₁ to C₂₀ alkyl group, a C₁ to C₂₀ alkoxy group, a phenyl group, anaphthyl group, a fluorenyl group, a spiro-fluorenyl group, abenzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group,an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinylgroup, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, aquinolinyl group, an isoquinolinyl group, a quinoxalinyl group, aquinazolinyl group, a carbazolyl group, and a triazinyl group, e3 is aninteger selected from 1, 2, and 3, e4 is an integer selected from 1, 2,3, and 4, e5 is an integer selected from 1, 2, 3, 4, and 5, e6 is aninteger selected from 1, 2, 3, 4, 5, and 6, e7 is an integer selectedfrom 1, 2, 3, 4, 5, 6, and 7, e8 is an integer selected from 1, 2, 3, 4,5, 6, 7, and 8, e9 is an integer selected from 1, 2, 3, 4, 5, 6, 7, 8,and 9, and * indicates a binding site to a neighboring atom.
 12. Thecondensed cyclic compound as claimed in claim 1, wherein: R₁ to R₁₄ areeach independently selected from a group represented by Formula 2, agroup represented by Formula 3, a hydrogen, a deuterium, —F, —Cl, —Br,—I, a hydroxyl group, a cyano group, a nitro group, an amino group, anamidino group, a hydrazine group, a hydrazone group, a carboxylic acidor a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acidor a salt thereof, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group,—Si(Q₁)(Q₂)(Q₃), a phenyl group, a naphthyl group, a pyridinyl group, apyrimidinyl group, and a triazinyl group, wherein Q₁ to Q₃ are eachindependently selected from a C₁-C₁₀ alkyl group, a C₁-C₁₀ alkoxy group,a phenyl group, and a naphthyl group, and Ar₁ to Ar₄ are eachindependently a group represented by one of the following Formulae 6-1to 6-40,

wherein, in Formulae 6-1 to 6-40, * indicates a binding site to aneighboring atom.
 13. The condensed cyclic compound as claimed in claim1, wherein the condensed cyclic compound represented by Formula 1 isrepresented by one of the following Formulae 1-1 to 1-8:

wherein, X₁, L₁, L₂, a₁, a₂, Ar₁ to Ar₄, and R₁ to R₁₄ in Formula 1-1 toFormula 1-8 are defined the same as X₁, L₁, L₂, a₁, a₂, Ar₁ to Ar₄, andR₁ to R₁₄ of Formulae 1 to
 3. 14. The condensed cyclic compound asclaimed in claim 1, wherein the condensed cyclic compound represented byFormula 1 is represented by one of the following Formulae 1-1(1) to1-1(4):

wherein, in Formulae 1-1(1) to 1-1(4), X₁, L₁, L₂, Ar₁ to Ar₄, R₁ to R₄,R₆ to R₁₂ and R₁₄ are defined the same as X₁, L₁, L₂, Ar₁ to Ar₄, R₁ toR₄, R₆ to R₁₂ and R₁₄ of Formulae 1 to
 3. 15. The condensed cycliccompound as claimed in claim 14, wherein: R₁ to R₄, R₆ to R₁₂, and R₁₄are each independently selected from a hydrogen, a deuterium, —F, —Cl,—Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group,an amidino group, a hydrazine group, a hydrazone group, a carboxylicacid or a salt thereof, a sulfonic acid or a salt thereof, a phosphoricacid or a salt thereof, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, aphenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group,and a triazinyl group, L₁ and L₂ are each independently a grouprepresented by one of the following Formulae 3-1 to 3-35,

wherein, in Formulae 3-1 to 3-35, Y₁ is O, S, C(Z₃)(Z₄), N(Z₅), orSi(Z₆)(Z₇); Z₁ to Z₇ are each independently selected from a hydrogen, adeuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine group, a hydrazonegroup, a carboxylic acid or a salt thereof, a sulfonic acid or a saltthereof, a phosphoric acid or a salt thereof, a C₁ to C₂₀ alkyl group, aC₁ to C₂₀ alkoxy group, a phenyl group, a naphthyl group, a fluorenylgroup, a spiro-fluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, apyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group,a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, anisoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, acarbazolyl group, and a triazinyl group, d1 is an integer selected from1, 2, 3, and 4, d2 is an integer selected from 1, 2, and 3, d3 is aninteger selected from 1, 2, 3, 4, 5, and 6, d4 is an integer selectedfrom 1, 2, 3, 4, 5, 6, 7, and 8, d5 is 1 or 2, and d6 is an integerselected from 1, 2, 3, 4, and 5, and * and *′ indicate binding sites toa neighboring atom, a1 and a2 are each independently 0, 1, or 2; and Ar₁to Ar₄ are each independently a group represented by one of thefollowing Formulae 5-1 to 5-43,

wherein, in Formulae 5-1 to 5-43, Y₃₁ is O, S, C(Z₃₃)(Z₃₄), N(Z₃₅), orSi(Z₃₆)(Z₃₇); Z₃₁ to Z₃₇ are each independently selected from ahydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyanogroup, a nitro group, an amino group, an amidino group, a hydrazinegroup, a hydrazone group, a carboxylic acid or a salt thereof, asulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, aC₁ to C₂₀ alkyl group, a C₁ to C₂₀ alkoxy group, a phenyl group, anaphthyl group, a fluorenyl group, a spiro-fluorenyl group, abenzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group,an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinylgroup, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, aquinolinyl group, an isoquinolinyl group, a quinoxalinyl group, aquinazolinyl group, a carbazolyl group, and a triazinyl group, e3 is aninteger selected from 1, 2, and 3, e4 is an integer selected from 1, 2,3, and 4, e5 is an integer selected from 1, 2, 3, 4, and 5, e6 is aninteger selected from 1, 2, 3, 4, 5, and 6, e7 is an integer selectedfrom 1, 2, 3, 4, 5, 6, and 7, e8 is an integer selected from 1, 2, 3, 4,5, 6, 7, and 8, e9 is an integer selected from 1, 2, 3, 4, 5, 6, 7, 8,and 9, and * indicates a binding site to a neighboring atom.
 16. Thecondensed cyclic compound as claimed in claim 1, wherein the compoundrepresented by Formula 1 is one of the following Compounds 1 to 104:


17. An organic light-emitting device, comprising: a first electrode; asecond electrode facing the first electrode; and an organic layerbetween the first electrode and the second electrode, the organic layerincluding an emission layer, wherein the organic layer includes thecondensed cyclic compound as claimed in claim
 1. 18. The organiclight-emitting device as claimed in claim 17, wherein the firstelectrode is an anode, the second electrode is a cathode, and theorganic layer includes: a hole transport region between the firstelectrode and the emission layer, the hole transport region including atleast one of a hole injection layer, a hole transport layer, a bufferlayer, and an electron blocking layer, and an electron transport regionbetween the emission layer and the second electrode, the electrontransport region including at least one selected from a hole blockinglayer, an electron transport layer, and an electron injection layer. 19.The organic light-emitting device as claimed in claim 17, wherein theemission layer includes the condensed cyclic compound.
 20. The organiclight-emitting device as claimed in claim 19, wherein the emission layerfurther includes a compound represented by the following Formula 301:Ar₃₀₁-[(L₃₀₁)_(xb1)-R₃₀₁]_(xb2)  <Formula 301> wherein in Formula 301,Ar₃₀₁ is selected from: a naphthalene, a heptalene, a fluorenene, aspiro-fluorenene, a benzofluorenene, a dibenzofluorenene, a phenalene, aphenanthrene, an anthracene, a fluoranthene, a triphenylene, a pyrene, achrysene, a naphthacene, a picene, a perylene, a pentaphene, and anindenoanthracene; a naphthalene, a heptalene, a fluorenene, aspiro-fluorenene, a benzofluorenene, a dibenzofluorenene, a phenalene, aphenanthrene, an anthracene, a fluoranthene, a triphenylene, a pyrene, achrysene, a naphthacene, a picene, a perylene, a pentaphene, and anindenoanthracene, each substituted with at least one selected from adeuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine group, a hydrazonegroup, a carboxylic acid or a salt thereof, a sulfonic acid or a saltthereof, a phosphoric acid or a salt thereof, a C₁-C₆₀ alkyl group, aC₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy, a C₃-C₁₀cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenylgroup, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀aryloxy, a C₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, amonovalent non-aromatic condensed polycyclic group, a monovalentnon-aromatic condensed heteropolycyclic group, and—Si(Q₃₀₁)(Q₃₀₂)(Q₃₀₃), in which Q₃₀₁ to Q₃₀₃ are each independentlyselected from a hydrogen, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group,a C₁-C₆₀ aryl group, and a C₁-C₆₀ heteroaryl group; each L₃₀ isindependently selected from a substituted or unsubstituted C₃-C₁₀cycloalkylene group, a substituted or unsubstituted C₁-C₁₀heterocycloalkylene group, a substituted or unsubstituted C₃-C₁₀cycloalkenylene group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenylene group, a substituted or unsubstituted C₆-C₆₀arylene group, a substituted or unsubstituted C₁-C₆₀ heteroarylenegroup, a substituted or unsubstituted divalent non-aromatic condensedpolycyclic group, and a substituted or unsubstituted divalentnon-aromatic condensed heteropolycyclic group; R₃₀₁ is selected from: aC₁-C₂₀ alkyl group and a C₁-C₂₀ alkoxy group; a C₁-C₂₀ alkyl group and aC₁-C₂₀ alkoxy group, each substituted with at least one selected from adeuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amino group, an amidino group, a hydrazine group, a hydrazonegroup, a carboxylic acid or a salt thereof, a sulfonic acid or a saltthereof, a phosphoric acid or a salt thereof, a phenyl group, a naphthylgroup, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenylgroup, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenylgroup, a pyrenyl group, a chrysenyl group, a pyridinyl group, apyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinylgroup, an isoquinolinyl group, a quinoxalinyl group, a quinazolinylgroup, a carbazolyl group, and a triazinyl group; a phenyl group, anaphthyl group, a fluorenyl group, a spiro-fluorenyl group, abenzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group,an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinylgroup, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, aquinolinyl group, an isoquinolinyl group, a quinoxalinyl group, aquinazolinyl group, a carbazol group, and a triazinyl group; and aphenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenylgroup, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenylgroup, an anthracenyl group, a pyrenyl group, a chrysenyl group, apyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group,a quinazolinyl group, a carbazolyl group and a triazinyl group, eachsubstituted with at least one selected from a deuterium, —F, —Cl, —Br,—I, a hydroxyl group, a cyano group, a nitro group, an amino group, anamidino group, a hydrazine group, a hydrazone group, a carboxylic acidor a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acidor a salt thereof, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a phenylgroup, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, abenzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group,an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinylgroup, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, aquinolinyl group, an isoquinolinyl group, a quinoxalinyl group, aquinazolinyl group, a carbazolyl group, and a triazinyl group; xb1 isselected from 0, 1, 2, and 3; and xb2 is selected from 1, 2, 3, and 4.